Carbamate derivative and agricultural/horticultural fungicide

ABSTRACT

It is to provide a novel fungicide having high controlling effects on plant diseases particularly on wheat powdery mildew and cucumber gray mold, without ill effects on crops. 
     A carbamate derivative represented by the general formula [I]                   
     {wherein X is a halogen atom, a C 1 -C 6  alkyl group or the like, n is 0 or an integer of from 1 to 4, R 1  is a C 1 -C 6  alkyl group, R 2  is a hydrogen atom, a C 1 -C 6  alkyl group or the like, R 3  is a hydrogen atom or a C 1 -C 6  alkyl group, G is an oxygen atom, a sulfur atom or the like, Y is a hydrogen atom, a C 1 -C 10  alkyl group, C 2 -C 10  alkenyl group or the like, and Q is a hydrogen atom, a C 1 -C 6  haloalkyl group, a phenyl group or the like} and an agricultural/horticultural fungicide containing the same as the active ingredient.

TECHNICAL FIELD

The present invention relates to a novel carbamate derivative and anagricultural/horticultural fungicide containing said derivative as theactive ingredient.

BACKGROUND ART

Heretofore, many carbamic acid derivatives have been reported, but ithas not been known that a carbamic acid derivative having an oxime ethergroup in a phenyl group as the compound of the present invention hasexcellent fungicidal activities.

The object of the present invention is to provide a novel carbamatederivative and an agricultural/horticultural fungicide containing thesame as the active ingredient.

DISCLOSURE OF THE INVENTION

The present inventors have conducted extensive studies to produce anovel agricultural/horticultural fungicide and as a result, have foundthat the carbamate derivative of the present invention (hereinafterreferred to as compound of the present invention) is a novel compoundnot disclosed in any literatures and have outstanding effects as anagricultural/horticultural fungicide, and have finally accomplished thepresent invention. Namely, the present invention resides in (1) acarbamate derivative represented by the general formula [I]:

{wherein X is a halogen atom, a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group,a C₁-C₆ haloalkyl group or a C₁-C₆ haloalkoxy group, n is 0 or aninteger of from 1 to 4, R¹ is a C₁-C₆ alkyl group, R² is a hydrogenatom, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group,a C₁-C₆ alkoxy group, a C₁-C₆ alkoxy C₁-C₆ alkyl group, a C₁-C₆alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a C₁-C₆ alkylcarbonylC₁-C₆ alkyl group or a benzyl group which may be substituted, R³ is ahydrogen atom or a C₁-C₆ alkyl group, G is an oxygen atom, a sulfur atomor a —NR⁴— group [wherein R⁴ is a hydrogen atom or a C₁-C₆ alkyl group],Y is a hydrogen atom, a C₁-C₁₀ alkyl group (said group may besubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, hydroxyl group, C₃-C₆ cycloalkyl group, C₁-C₆ alkoxygroup, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylaminogroup, C₁-C₆ alkylthio group, C₁-C₆ alkylsulfinyl group, carboxyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, C₁-C₆ alkoxyiminogroup or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ which are the same ordifferent, is a hydrogen atom or a C₁-C₆ alkyl group)), a C₂-C₁₀ alkenylgroup (said group may be substituted by the same or different at leastone halogen atom, cyano group, nitro group, hydroxyl group, C₁-C₆ alkoxygroup, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylaminogroup, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonylgroup, C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶ (wherein each of R⁵ andR⁶ which are the same or different, is a hydrogen atom or a C₁-C₆ alkylgroup)), a C₂-C₁₀ alkynyl group (said group may be substituted by thesame or different at least one halogen atom, cyano group, nitro group,cycloalkyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group)), aC₃-C₆ cycloalkyl group (said group may be substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, C₁-C₆alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶ (whereineach of R⁵ and R⁶ which are the same or different, is a hydrogen atom ora C₁-C₆ alkyl group)), a C₃-C₆ cycloalkenyl group (said group may besubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, hydroxylgroup, C₂-C₆ alkynyl group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkoxy group, C₁-C₆ alkylthio group,C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonylgroup or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ which are the same ordifferent, is a hydrogen atom or a C₁-C₆ alkyl group)), a phenacyl group(said group may be substituted by the same or different at least onehalogen atom, C₁-C₆ alkyl group, C₁-C₆ alkoxy group, C₁-C₆ haloalkylgroup, C₁-C₆ alkylcarbonyl group or C₁-C₆ alkoxycarbonyl group), an arylgroup (said group may be substituted by the same or different at leastone halogen atom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆alkenyl group, C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group,amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group,C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group,C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ whichare the same or different, is a hydrogen atom or a C₁-C₆ alkyl group)),a heteroaryl group (said group may be substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, C₁-C₆alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶ (whereineach of R⁵ and R⁶ which are the same or different, is a hydrogen atom ora C₁-C₆ alkyl group)), an aryl-C₁-C₆ alkyl group (the aryl in said groupmay be substituted by the same or different at least one halogen atom,cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, phenoxy group which may be substituted, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆haloalkoxy group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group,C₁-C₆ alkoxyimino C₁-C₆ alkyl group or C(O)NR⁵R⁶ (wherein each of R⁵ andR⁶ which are the same or different, is a hydrogen atom or a C₁-C₆ alkylgroup)), an aryl-C₂-C₆ alkenyl group (the aryl in said group may besubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group)) or aheterocyclic-C₁-C₆ alkyl group (the heterocycle in said group may besubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group or C(O)NR⁵R⁶ (wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group)), andQ is a hydrogen atom, a haloalkyl group, a cyano group, a C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl group, a C₁-C₄ alkylthio group, a C₁-C₄alkylsulfinyl group, a C₁-C₄ alkylsulfonyl group or a phenyl group (saidgroup may be substituted by at least one halogen atom, cyano group,nitro group, C₁-C₄ alkyl group, C₂-C₄ alkenyl group, C₂-C₄ alkynylgroup, hydroxyl group, C₁-C₄ alkoxy group, C₁-C₄ haloalkyl group, C₁-C₄haloalkoxy group, C₁-C₄ alkylcarbonyl group or C₁-C₄ alkoxycarbonylgroup)}, and (2) an agricultural/horticultural fungicide containing thesame as the active ingredient.

Symbols and terms used in the present specification will be explained.

The halogen atom is a fluorine atom, a chlorine atom, a bromine atom oran iodine atom.

A notation such as C₁-C₁₀ indicates that the carbon number of asubstituent following this notation is from 1 to 10 in this case.

The C₁-C₆ alkyl group is a straight chain or branched chain alkyl groupand may, for example, be methyl, ethyl, n-propyl, iso-propyl, n-butyl,iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl,n-hexyl, 1,1-dimethylpropyl or 1,1-dimethylbutyl.

The C₁-C₁₀ alkyl group may, for example, be the above-mentioned C₁-C₆alkyl group, or a group such as heptyl, octyl, 1,1-diethylbutyl, nonylor decyl.

The C₃-C₆ cycloalkyl group may, for example, be a group such ascyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

The C₃-C₆ cycloalkenyl group may, for example, be a group such as1-cyclopenten-1-yl, 2-cyclopenten-1-yl, 1-cyclohexen-1-yl or2-cyclohexen-1-yl.

The C₁-C₆ haloalkyl group is a straight chain or branched chain alkylgroup substituted by a halogen atom and may, for example, be a groupsuch as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl,trifluoromethyl or pentafluoroethyl.

The C₂-C₁₀ alkenyl group is a straight chain or branched chain alkenylgroup and may, for example, be vinyl, 1-propenyl, 2-propenyl,isopropenyl, 1-butenyl, 2-butenyl, 1-hexenyl or 1-octenyl.

The C₂-C₁₀ alkynyl group is a straight chain or branched chain alkynylgroup and may, for example, be a group such as ethynyl, 1-propynyl,2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-1-pentynyl or3-methyl-1-pentynyl.

The C₁-C₆ alkoxy group is an alkyloxy group wherein the alkyl moiety hasthe above meaning and may, for example, be a group such as methoxy,ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy,tert-butoxy, n-pentyloxy, isopentyloxy or n-hexyloxy.

The C₁-C₆ haloalkoxy group is a haloalkyloxy group wherein the haloalkylmoiety has the above meaning and may, for example, be a group such asfluoromethoxy, difluoromethoxy, trifluoromethoxy or pentafluoroethoxy.

The C₁-C₆ alkoxyimino group is an alkoxyimino group wherein the alkoxymoiety has the above meaning and may, for example, be a group such asmethoxyimino.

The C₁-C₆ alkoxyimino C₁-C₆ alkyl group is an alkoxyiminoalkyl groupwherein the alkoxy moiety and the alkyl moiety have the above meaningsand may, for example, be a group such as 1-methoxyiminoethyl.

The C₁-C₆ alkylcarbonyl group is an alkylcarbonyl group wherein thealkyl moiety has the above meaning, and may, for example, be a groupsuch as acetyl, propionyl, butyryl, isobutyryl, pivaloyl or hexanoyl.

The C₁-C₆ alkoxycarbonyl group is an alkoxycarbonyl group wherein thealkoxy moiety has the above meaning and may, for example, be a groupsuch as methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl orhexyloxycarbonyl.

The C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group is an alkylcarbonylalkyl groupwherein the alkyl moiety has the above meaning and may, for example, bea group such as a 2-oxypropyl group, a 3-oxobutyl group, a 3-oxopentylgroup or a 3,3-dimethyl-2-oxobutyl group.

The aryl group is an aromatic hydrocarbon group and may, for example, bea group such as phenyl, 1-naphthyl or 2-naphthyl.

The heterocyclic-C₁-C₆ alkyl group is a 3- to 10-membered cycle whereinthe alkyl moiety is —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH(Me)—, —C(Me)₂—,—CH(Et)— or the like, and the heterocyclic moiety is constituted of from2 to 9 carbon atoms, from 0 to 3 nitrogen atoms, from 0 to 3 oxygenatoms and from 0 to 3 sulfur atoms, and may, for example, be a groupsuch as pyrrolyl, furyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl,imidazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl,pyrazinyl, triazinyl, indolyl, benzofuryl, benzothienyl, benzimidazolyl,benzoxazolyl, benzothiazolyl, quinolyl, isoquinolyl, morpholino,oxyranyl or dioxacyclopentyl.

The heteroaryl group is a 5- to 10-membered heterocyclic aromatic ringgroup constituted of from 2 to 9 carbon atoms, from 0 to 3 nitrogenatoms, from 0 to 3 oxygen atoms and from 0 to 3 sulfur atoms, and may,for example, be a heterocycle such as pyrrolyl, furyl, thienyl,pyrazolyl, isoxazolyl, isothiazolyl, imidazolyl, oxazolyl, thiazolyl,pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl,benzofuryl, benzothienyl, benzimidazolyl, benzoxazolyl, benzothiazolyl,quinolyl or isoquinolyl.

The C₁-C₆ alkoxy C₁-C₆ alkyl group is a group wherein the alkyl moietyand the alkoxy moiety have the above meanings and may, for example, be agroup such as methoxymethyl, ethoxymethyl, isopropoxymethyl,pentyloxymethyl, methoxyethyl or butoxyethyl.

The mono C₁-C₆ alkylamino group is a group wherein the alkyl moiety hasthe above meaning and may be a group such as methylamino, ethylamino,isopropylamino, butylamino or tert-butylamino.

The di-C₁-C₆ alkylamino group is a group wherein each of the alkylmoieties which are the same or different, has the above meaning, andmay, for example, be a group such as dimethylamino, diethylamino,methylethylamino, methylisopropylamino or dihexylamino.

The C₁-C₆ alkylthio group is a group wherein the alkyl moiety has theabove meaning and may be a group such as methylthio, ethylthio,isopropylthio, butylthio or hexylthio.

The C₁-C₆ alkylsulfinyl group is a group wherein the alkyl moiety hasthe above meaning and may be a group such as methylsulfinyl,ethylsulfinyl, isopropylsulfinyl, butylsulfinyl or hexylsulfinyl.

The C₁-C₆ alkylsulfonyl group is a group wherein the alkyl moiety hasthe above meaning and may be a group such as methylsulfonyl,ethylsulfonyl, isopropylsulfonyl, butylsulfonyl or hexylsulfonyl.

The aryl C₁-C₆ alkyl group is a group wherein the aryl moiety has theabove meaning and the alkyl moiety is —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—,—CH(Me)—, —C(Me)₂—, —CH(Et)— or the like.

The aryl C₁-C₆ alkenyl group is a group wherein the aryl moiety has theabove meaning and the alkenyl moiety is —CH═CH—, —CH═CHCH₂—, —C(Me)═CH—,—CH(Et)═(CH)—, —C(Me)═CHCH₂— or the like.

The heteroaryl C₁-C₆ alkyl group is a group wherein the heteroarylmoiety has the above meaning and the alkyl moiety is —CH₂—, —CH₂CH₂—,—CH₂CH₂CH₂—, —CH(Me)—, —(Me)₂—, —CH(Et)— or the like.

BEST MODE FOR CARRYING OUT THE INVENTION

Now, specific examples of the compound of the present inventionrepresented by the general formula [I] will be described in Tables 1 to13. However, the compound of the present invention is not limited tosuch compounds. Here, the compound Nos. will be referred to in thesubsequent description.

Symbols in the Tables have the following meanings respectively. Merepresents a methyl group, Et represents an ethyl group, Pr represents an-propyl group, Pr-i represents an iso-propyl group, Bu represents an-butyl group, Bu-i represents an iso-butyl group, Bu-s represents asec-butyl group, Bu-t represents a tert-butyl group, Hex represents an-hexyl group, Pr-c represents a cyclopropyl group, Pen-c represents acyclopentyl group, Hex-c represents a cyclohexyl group, and Phrepresents a phenyl group. Further, Ph(4-Cl) represents a 4-chlorophenylgroup for example.

Some of the compounds of the present invention represented by thegeneral formula [I] have one or from 2 to 3 double bonds relating to E/Zisomers in their molecules, and with respect to such compounds, E/Zisomer mixtures are present. Pure individual E-forms and Z-forms andtheir mixtures are also included in the compounds of the presentinvention. The following pairs of compounds are geometrical isomersrelating to oxime portion double bond (A-80 and A-206, A-84 and A-207,A-85 and A-208, A-86 and A-209, A-286 and A-448).

TABLE 1

m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰) A-1  OMe H H H H H H CN Me 84-87 A-2  O Me H H Cl H H H CN H 1.5601 A-3  O MeH H Cl H H H CN Me 104-107 A-4  O Me H H Cl H H H CN CH₂CH═CH₂ A-5  O MeH H Cl H H H CN CH₂C≡CH A-6  O Me H H Cl H H H CN CH₂COOEt A-7  O Me H HCl H H H CN CH₂Ph 113-115 A-8  O Me H H Cl H H H CN CH₂Ph(2-Cl) 115-118A-9  O Me H H Cl H H H CN CH₂Ph(3-Cl) 127-130 A-10 O Me H H Cl H H H CNCH₂Ph(4-Cl) A-11 O Me H H Cl H H H CN CH₂Ph(2-Me) 113-116 A-12 O Me H HCl H H H CN CH₂Ph(3-Me) A-13 O Me H H Cl H H H CN CH₂Ph(4-Me) A-14 O MeH H Cl H H H CN CH₂Ph(2-CF₃) A-15 O Me H H Cl H H H CN CH₂Ph(3-CF₃) A-16O Me H H Cl H H H CN CH₂Ph(4-CF₃) A-17 O Me H H Cl H H H CN Me A-18 O MeH H Cl H H H CN Et A-19 O Me H H Cl H H H CN CH₂CH═CH₂ A-20 O Me H H MeH H H CN CH₂Ph 104-107 A-21 O Me H H Me H H H CN CH₂Ph(2-Cl) 120-123A-22 O Me H H Me H H H CN CH₂Ph(3-Cl) A-23 O Me H H Me H H H CNCH₂Ph(4-Cl) A-24 O Me H H Me H H H CN CH₂Ph(2-Me) A-25 O Me H H Me H H HCN CH₂Ph(3-Me) A-26 O Me H H Me H H H CN CH₂Ph(4-Me) A-27 O Me H H Me HH H CN CH₂Ph(2-CF₃) A-28 O Me H H Me H H H CN CH₂Ph(3-CF₃) A-29 O Me H HMe H H H CN CH₂Ph(4-CF₃) A-30 O Me H H Me H H H CN

158-161 A-31 O Me H H Cl H H H CN

162-165 A-32 O Me H H H H H H H H A-33 O Me H H H H H H H Me A-34 O Me HH H H H H H Et A-35 O Me H H H H H H H Pr A-36 O Me H H H H H H H CH₂PhA-37 O Me H H H H H H Me CH₂CH═CH₂ 1.5421 A-38 O Me H H H H H H Me CH₂Ph1.5742 A-39 O Me H H H H H H Me Et 1.5389 A-40 O Me H H H H H H Me Me1.5475 A-41 O Me H H H H H H Ph CH₂CH═CH₂ 1.5869 m.p.: Melting point RI:Refractive index

TABLE 2 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-42 O Me H H H H H H Ph Me 1.5939 A-43 O Me H H H H H H Ph Et 1.5795A-44 O Me H H H H H H Ph(4-Cl) Et A-45 O Me H H Cl H H H Me H 124-127A-46 O Me H H Cl H H H Me Me 69-72 A-47 O Et H H Cl H H H Me Me A-48 OPr H H Cl H H H Me Me A-49 O Me H H Cl H H H Me Et 71-74 A-50 O Me H HCl H H H Me Pr 1.5433 A-51 O Me H H Cl H H H Me Pr-i 1.6382 A-52 O Me HH Cl H H H Me Bu 38-40 A-53 O Me H H Cl H H H Me Bu-s 1.5332 A-54 O Me HH Cl H H H Me Bu-i 1.5338 A-55 O Me H H Cl H H H Me Bu-t 1.5269 A-56 OMe H H Cl H H H Me CH₂Pr-c 1.5531 A-57 O Me H H Cl H H H Me Pen-c A-58 OMe H H Cl H H H Me CH₂CH═CH₃ 69-72 A-59 O Me H H Cl H H H MeCH₂C(Me)═CH₂ A-60 O Me H H Cl H H H Me CH₂CH═CHCO₂Et A-61 O Me H H Cl HH H Me CH₃CH≡CH 85-88 A-62 O Me H H Cl H H H Me CH₂CH₂CH₂Ph 1.5597 A-63O Me H H Cl H H H Me CH₂COOEt 1.5402 A-64 O Me H H Cl H H H MeCH₂COOBu-t 1.5211 A-65 O Me H H Cl H H H Me CH₂CON(Me)₂ A-66 O Me H H ClH H H Me CH₂CO₃H A-67 O Me H H Cl H H H Me CH₂OMe 62-65 A-68 O Me H H ClH H H Me CH₂SMe A-69 O Me H H Cl H H H Me CH₂SOMe A-70 O Me H H Cl H H HMe CH₂CF₃ 91-94 A-71 O Me H H Cl H H H Me CH₂CN 93-96 A-72 O Me H H Cl HH H Me CH═CH₃ A-73 O Me H H Cl H H H Me Ph 87-90 A-74 O Me H H Cl H H HMe Ph(3-Cl) A-75 O Me H H Cl H H H Me Ph(4-Cl) A-76 O Me H H Cl H H H MePh(3-Me) A-77 O Me H H Cl H H H Me Ph(4-Me) A-78 O Me H H Cl H H H MePh(3-CF₃) A-79 O Me H H Cl H H H Me Ph(4-CF₃) A-80 O Me H H Cl H H H MeCH₂Ph 65-68 A-81 O Me H H Cl H H H Me CH₂Ph(2-F) 80-82 A-82 O Me H H ClH H H Me CH₂Ph(3-F) 88-91 A-83 O Me H H Cl H H H Me CH₂Ph(4-F) 101-103A-84 O Me H H Cl H H H Me CH₂Ph(2-Cl) 88-91 A-85 O Me H H Cl H H H MeCH₂Ph(3-Cl) 68-71 A-86 O Me H H Cl H H H Me CH₂Ph(4-Cl) 103-106 A-87 OMe H H Cl H H H Me CH₂Ph(2-Br) 80-83 A-88 O Me H H Cl H H H MeCH₂Ph(3-Br) 79-81 A-89 O Me H H Cl H H H Me CH₂Ph(4-Br) 108-110 A-90 OMe H H Cl H H H Me CH₂Ph(2-Me) 88-91 A-91 O Me H H Cl H H H MeCH₂Ph(3-Me) 1.5722 A-92 O Me H H Cl H H H Me CH₂Ph(4-Me)  97-100 A-93 OMe H H Cl H H H Me CH₂Ph(2-OMe) 116-119 A-94 O Me H H Cl H H H MeCH₂Ph(3-OMe) 1.5789 A-95 O Me H H Cl H H H Me CH₂Ph(4-OMe) 1.5762 A-96 OMe H H Cl H H H Me CH₂Ph(2-Bu-t)

TABLE 3 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-97  O Me H H Cl H H H Me CH₂Ph(3-Bu-t) A-98  O Me H H Cl H H H MeCH₂Ph(4-Bu-t) 1.5552 A-99  O Me H H Cl H H H Me CH₂Ph(2-CF₃) 81-83 A-100O Me H H Cl H H H Me CH₂Ph(3-CF₃) 1.5329 A-101 O Me H H Cl H H H MeCH₂Ph(4-CF₃) 117-118 A-102 O Me H H Cl H H H Me CH₂Ph(3-CN) 79-82 A-103O Me H H Cl H H H Me CH₂Ph(4-CN) 121-124 A-104 O Me H H Cl H H H MeCH₂Ph(4-NO₂) A-105 O Me H H Cl H H H Me CH₂Ph(4-COOMe) 124-227 A-106 OMe H H Cl H H H Me CH₂Ph(4-OCF₃) 104-107 A-107 O Me H H Cl H H H MeCH₂Ph(3-OPh) A-108 O Me H H Cl H H H Me CH₂Ph(4-OPh) A-109 O Me H H Cl HH H Me

172-176 A-110 O Me H H Cl H H H Me

A-111 O Me H H Cl H H H Et Et 79-82 A-112 O Me H H Me H H H H CH₂Ph65-68 A-113 O Me H H Me H H H Me CH₂Ph 92-95 A-114 NH Me H H Me H H H HCH₂Ph A-115 NH Me H H Me H H H H Me A-116 NMe Me H H Me H H H H Me A-117S Me H H Me H H H H Pr A-118 O Me H H Cl Me H H H CH₂Ph A-119 O Me Me HCl Me H H H Pr A-120 O Me Me H Cl Me H H H CH₂Ph A-121 O Me CH₂OMe H ClMe H H Me Pr A-122 O Me CH₂OMe H Cl Me H H Me CH₂Ph A-123 O Me CH₂CH═CH₂H Cl Me H H Me Pr A-124 O Me CH₂CH═CH₂ H Cl Me H H Me CH₂Ph A-125 O MeCH₂C≡CH H Cl H H H Me CH₂Ph A-126 O Me CH₂C≡CH H Cl H H H Me Et A-127 OMe CH₂COMe H Cl H H H Me CH₂Ph A-128 O Me CH₂COMe H Cl H H H Me Me A-129O Me CO₂Me H Cl H H H Me CH₂Ph A-130 O Me CO₂Me H Cl H H H Me Ph A-131 OMe COMe H CL Me H H Me Pr A-132 O Me COMe H Cl Me H H Me CH₂Ph A-138 OMe OMe H Cl Me H H Me Pr A-134 O Me OMe H Cl Me H H Me CH₂Ph A-135 O MeH H Cl Me H H Me H A-136 O Me H H Cl Me H H Me Me A-137 O Me H H Cl Me HH Me Et A-138 O Me H H Cl Me H H Me Pr A-139 O Me H H Cl Me H H Me Pr-iA-140 O Me H H Cl Me H H Me Bu A-141 O Me H H Cl Me H H Me Bu-s A-142 OMe H H Cl Me H H Me Bu-i A-143 O Me H H Cl Me H H Me Bu-t A-144 O Me H HCl Me H H Me CH₂CH═CH₂ A-145 O Me H H Cl Me H H Me CH₂C≡CH

TABLE 4 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-146 O Me H H Cl Me H H Me CH₂CN A-147 O Me H H Cl Me H H Me CH₂COOMeA-148 O Me H H Cl Me H H Me CH₂COOEt A-149 O Me H H Cl Me H H Me CH₂CO₂HA-150 O Me H H Cl Me H H Me CH₂Ph 1.5821 A-151 O Me H H Cl Me H H MeCH₂Ph(3-F) 64-67 A-152 O Me H H Cl Me H H Me CH₂Ph(4-F) 85-88 A-153 O MeH H Cl Me H H Me CH₂Ph(3-Cl) 88-91 A-154 O Me H H Cl Me H H MeCH₂Ph(4-Cl) 107-110 A-155 O Me H H Cl Me H H Me CH₂Ph(3-Me) 1.5761 A-156O Me H H Cl Me H H Me CH₂Ph(4-Me) 75-78 A-157 O Me H H Cl Me H H MeCH₂Ph(3-OMe) 73-76 A-158 O Me H H Cl Me H H Me CH₂Ph(4-OMe) 1.5788 A-159O Me H H Cl Me H H Me CH₂Ph(3-CF₃) 88-89 A-160 O Me H H Cl Me H H MeCH₂Ph(4-CF₃) 100-103 A-161 O Me H H Me H Me Me Me CH₂CO₂Me A-162 O Me HH Me H Me Me Me CH₂C≡CH A-163 O Me H H Cl H H Cl Me CH₂CH═CH₂ A-164 O MeH H Cl H H Cl Me CH₂Ph A-165 O Me H H OMe H H H Me Et A-166 O Me H H OMeH H H Me Pr-i A-167 O Me H H CF₃ H H H Me Me A-168 O Me H H CF₃ H H H MeCH₂Ph A-169 O Me H H OCF₃ H H H Me Me A-170 O Me H H OCF₃ H H H Me CH₂PhA-171 O Me H H Cl H H H CF₃ Me A-172 O Me H H Cl H H H CF₃ CH₂Ph A-173 OMe H H Cl H H H Pr-c CH₂CN A-174 O Me H H Cl H H H Pr-c CH₂OMe A-175 OMe H H Cl H H H Me CH₂OH A-176 O Me H H Me H H H Me CH₂OH A-177 O Me H HCl H H H Me CH₂CH₂NH₂ A-178 O Me H H Me H H H Me CH₂CH₂NH₂ A-179 O Me HH Cl H H H Me CH₂CH₂N(Me)₂ A-180 O Me H H Me H H H Me CH₂CH₂N(Me)₂ A-181O Me H H Cl H H H Me CH₃COMe A-182 O Me H H Me H H H Me CH₃COMe A-183 OMe H H Cl H H H Me CH₂CONHMe A-184 O Me H H Me H H H Me CH₂CONHMe A-185O Me H H Cl H H H Me CH₂CH═CCl₂ A-186 O Me H H Me H H H Me CH₂CH═CCl₂A-187 O Me H H Cl H H H Me CH₂(CH₂)₂CH═CH₂ A-188 O Me H H Me H H H MeCH₂(CH₂)₂CH═CH₂ A-189 O Me H H Cl H H H Me CH₂CH═CHMe 1.5529 A-190 O MeH H Me H H H Me CH₂CH═CHMe A-191 O Me H Me Cl H H H Me CH₂Ph A-192 O MeH Me Cl H H H Me Pr A-193 O Me H Me Me H H H Me CH₂Ph A-194 O Me H Me MeH H H Me Pr A-195 O Me H H Cl H H H Me CH₂C≡CCH₂CH₂OMe A-196 O Me H H ClH H H Me CH₂C≡CCH₂OH A-197 O Me H H Cl H H H Me CH₂C≡CC(O)Me

TABLE 5 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-198 O Me H H Cl H H H Me CH₂CH₂CH═CH₂ 1.5481 A-199 O Me H H H H H H MeCH₂CH═CHCH₂OH A-200 O Me H H H H H H Me CH₂CH═CHCH₂OMe A-201 O Me H H ClH H H Me CH₂CH═CHPh 83-88 A-202 O Me H H H H H H MeCH₂CH═CHPh(3-OMe,4-OH) A-203 O Me H H H H H H Me CH₂CH═CHPh(4-Cl) A-204O Me H H H H H H Me CH₂CH═CHPh(2-Me) A-205 O Me H H H H H H MeCH₂CH═CHPh(3-NO₂) A-206 O Me H H Cl H H H Me CH₂Ph 1.5769 A-207 O Me H HCl H H H Me CH₂Ph(2-Cl) 1.5819 A-208 O Me H H Cl H H H Me CH₂Ph(3-Cl)60-62 A-209 O Me H H Cl H H H Me CH₂Ph(4-Cl) 91-94 A-210 O Me H H H H EtH Me CH₂Ph A-211 O Me H H H H Pr-i H Me CH₂Ph A-212 O Me H H H H Hex HMe CH₂Ph A-213 O Me H H OEt H H H Me CH₂Ph(4-Cl) A-214 O Me H H OPr-i HH H Me CH₂Ph(4-Cl) A-215 O Me H H Cl H H H Me

1.6189 A-216 O Me H H Cl H H H Me CH(Me)Ph 1.5745 A-217 O Me H H Cl H HH Me CH₂Ph(2-OCF₃) 72-74 A-218 O Me H H Cl H H H Me CH₂Ph(3-OCF₃) 73-74A-219 O Me CH₂Ph(2-Cl) H Me H H H CN CH₂Ph(2-Cl) 1.5883 A-220 O Me H HCl H H H Me CH₂Ph(2-CN) 89-92 A-221 O Me H H Br H H H Me CH₂Ph(2-Cl)A-222 O Me H H I H H H Me CH₂Ph(2-Cl) A-223 O Me H H H H Cl H MeCH₂Ph(2-Cl) A-224 O Me H H Cl H Cl H Me CH₂Ph(2-Cl) A-225 O Me H H Cl HH H Me

105-108 A-226 O Me H H Cl H H H Me

A-227 O Me H H Cl H H H Me

85-86 A-228 O Me H H Cl H H H Me

81-84 A-229 O Me H H Cl H H H Me

1.5532 A-230 O Me H H Cl H H H Me CH₂C≡CPen-c A-231 O Me H H Cl H H H Me

A-232 O Me H H Cl H H H Me

TABLE 6 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-233 O Me H H Cl H H H Me

A-234 O Me H H Cl H H H Me CH₂CH₂N(Me)₂ 1.5461 A-235 O Me H H Cl H H HMe

128-130 A-236 O Me H H Cl H H H Me

A-237 O Me H H Cl H H H Me

130-131 A-238 O Me H H Cl H H H Me

A-239 O Me H H Cl H H H Me

A-240 O Me H H Cl H H H Me

1.5581 A-241 O Me H H Cl H H H Me

1.5541 A-242 O Me H H Cl H H H Me CH₂Hex-c 86-87 A-243 O Me H H Cl H H HMe

A-244 O Me H H Cl H H H Me

A-245 O Me H H Cl H H H Me

144-146 A-246 O Me H H Cl H H H Me

A-247 O Me H H Cl H H H Me

A-248 O Me H H Cl H H H Me

88-91 A-249 O Me H H Cl H H H Me

TABLE 7 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-250 O Me H H H H H H Me

A-251 O Me H H Cl H H H Me —(CH₂)₆Me 1.5272 A-252 O Me H H Cl H H H MeCH₂Ph(2,3-(Cl)₂) 103-106 A-253 O Me H H Cl H H H Me CH₂Ph(2,4-(Cl)₂)119-120 A-254 O Me H H Cl H H H Me CH₂Ph(2,5-(Cl)₂) 96-99 A-255 O Me H HCl H H H Me CH₂Ph(2,5-(Cl)₂) 140-143 A-256 O Me H H Cl H H H MeCH₂Ph(3,4-(Cl)₂) 94-96 A-257 O Me H H Cl H H H Me CH₂Ph(3,5-(Cl)₂) 96-98A-258 O Me H H Cl H H H Me CH₂Ph(2,5-(Me)₂) 88-91 A-259 O Pr-i H H H H HH Me CH₂Ph(2-Cl) A-260 O Me H Pr-i Cl H H H Me CH₂Ph(2-Cl) A-261 O Me HH Cl H H H Me

168-171 A-262 O Me H H Cl H H H Me

A-263 O Me H H Cl H H H Me

A-264 O Me H H Cl H H H Me

A-265 O Me H H Cl H H H Me

A-266 O Me H H Cl H H H Me CH₂Ph(3-NO₂) 1.5811 A-267 O Me H H Cl H H HMe CH₂Ph(4-COMe) 121-124 A-268 O Me H H CH₂Br H H H Me CH₂Ph(2-CH₂)A-269 O Me H H Cl H H H Me CH₂Ph(8-COMe) 1.5829 A-270 O Me H H H H CH₂ClH Me CH₂Ph(2-CH₂) A-271 O Me H H OCH₂Cl H H H Me CH₂Ph(4-CH₂) A-272 O MeH H Cl H H H Me

105-108 A-273 O Me H H Cl H H H H Pr-i 1.5881 A-274 O Me H H Cl H H HHex-c CH₂Ph A-275 O Me H H H H H H SMe CH₂Ph A-276 O Me H H H H H HS(O)Me CH₂Ph A-277 O Me H H Cl H H H CN CH₂CH₂Ph 87-90 A-278 O Me H H ClH H H Me CH₂Ph(3-CO₂Me) 70-73 A-279 O Me H H Cl H H H MeCH₂Ph(3,5-(Me)₂) 79-82 A-280 O Me H H H H H H Me CH₂CH₂NO₂ A-281 O Me HH Cl H H H Me CH₂CH₂NHEt A-282 O Me H H Cl H H H Me

153-156 A-283 O Me H H Cl H H H Me

122-125

TABLE 8 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-284 O Me H H Cl H H H Me

A-285 O Me H H Cl H H H Me

76-78 A-286 O Me H H Cl H H H Me

93-96 A-287 O Me H H Cl H H H CN

103-106 A-288 O Me H H Cl H H H Et

1.5659 A-289 O Me H H Cl H H H SO₂Me CH₂Ph(2-Cl) 1.5713 A-290 O Me H HCl H H H SO₂Me

1.5681 A-291 O Me H H Cl H H H Me CH₂Ph(3-C(Me)═NOMe) 1.5869 A-292 O MeH H Cl H H H Et CH₂COMe 1.5421 A-293 O Me H H Cl H H H Et CH₂C(Me)═NOMe1.5262 A-294 O Me H H Me H H H Me CH₂Ph(2-Cl) 103-106 A-295 O Me H H MeH H H Me CH₂Ph(2-Me) 95-98 A-296 O Me H H Cl H H H Et CH₂Ph(2-Cl) 74-77A-297 O Me H H Cl H H H Et CH₂Ph(2-CF₃) 1.5238 A-298 O Me H H Cl H H HEt CH(Me)COMe 1.5258 A-299 O Me H H Cl H H H Et CH(Me)C(Me)═NOMe 1.5241A-300 O Me H H Cl H H H Et CH(Me)C(Me)═NOEt 1.5218 A-301 O Me H H Cl H HH Me CH₂C≡CCH₂NH₂ A-302 O Me H H Cl H H H Me CH₂C≡CCO₂Me A-303 O Me H HCl H H H Et CH₂Ph 1.5757 A-304 O Me H H Cl H H H Et CH₂Ph(3-OMe) 1.5649A-305 O Me H H Cl H H H Et

1.5691 A-306 O Me H H Cl H H H Me

121-124 A-307 O Me H H Cl H H H Me

A-308 O Me H H Cl H H H Me

A-309 O Me H H Cl H H H Me CH(Me)Ph(2-Cl) 1.5749 A-310 O Me H H Cl H H HMe CH(Me)Ph(3-Cl) 1.5792 A-311 O Me H H Cl H H H Me CH(Me)Ph(4-Cl) 99-102 A-312 O Me H H Cl H H H Me CH(Me)Ph(3-OMe) 1.5734 A-313 O Me H HCl H H H Me CH(Me)Ph(3-CF₃) 1.5369 A-314 O Me H H Me H H H MeCH₂Ph(2-CF₃) 107-110 A-315 O Me H H Me H H H Me CH₂Ph(3-OMe) 1.5621A-316 O Me H H H H H H Me Ph(3,5-Cl₂) A-317 O Me H H H H H H MePh(2-NO₂) A-318 O Me H H H H H H Me Ph(3-Br)

TABLE 9 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-319 O Me H H H H H H Me Ph(4-F) A-320 O Me H H Cl Cl H H MeCH₂Ph(2-Me) 89-92 A-321 O Me H H Cl Cl H H Me CH₂Ph(2-Cl) 118-121 A-322O Me CH₂Ph(3-OMe) H Me H H H Me CH₂Ph(3-OMe) 1.5653 A-323 O Me H H F H HH Me CH₂Ph 59-62 A-324 O Me H H F H H H Me CH₂Ph(2-F) 63-64 A-325 O Me HH F H H H Me CH₂Ph(2-Cl) 66-67 A-326 O Me H H F H H H Me CH₂Ph(2-Br)56-57 A-327 O Me H H F H H H Me CH₂Ph(2-Me) 80-81 A-328 O Me H H F H H HMe CH₂Ph(2-CF₃) 73-74 A-329 O Me H H F H H H Me CH₂Ph(3-OMe) 1.5651A-330 O Me H H F H H H Me

81-83 A-331 O Me H H Cl Me H H Me CH₂Ph(2-Cl) 103-104 A-332 O Me H H ClCl H H Me

1.5823 A-333 O Me H H Me H H H Me

1.5641 A-334 O Me H H Cl H H H Me

82-85 A-335 O Me H H Cl H H H Me

A-336 O Me H H Cl H H H Me

A-337 O Me H H H H H H Me

A-338 O Me H H H H H H Me CH₂Ph(2-Cl) 1.5711 A-339 O Me H H H H H H MeCH₂Ph(3-Cl) 1.5788 A-340 O Me H H H H H H Me CH₂Ph(4-Cl) 72-75 A-341 OMe H H Cl H H H Pr-c CH₂Ph(2-Cl) 1.5781 A-342 O Me H H Me H H H MeCH₂Ph(2-F) 93-96 A-343 O Me H H H H H H Me CH₂Ph(2-Me) 1.5739 A-344 O MeH H H H H H Me CH₂Ph(3-Me) 1.5729 A-345 O Me H H H H H H Me CH₂Ph(4-Me)75-78 A-346 O Me H H Cl Me H H Me CH₂Ph(2-Me) 82-85 A-347 O Me H H Cl MeH H Me CH₂Ph(2-CF₃) 71-73 A-348 O Me H H H H H H Me CH₂Ph(2-CF₃) 1.5399A-349 O Me H H H H H H Me CH₂Ph(3-CF₃) 1.5349 A-350 O Me H H H H H H MeCH₂Ph(4-CF₃) 1.5291 A-351 O Me H H H H H H Me Ph(3-CO₂Me) A-352 O Me H HR H H H Me Ph(2-NO₂,4-Cl) A-353 O Me H H H H H H Me Ph(3-Cl,5-OMe) A-354O Me H H Cl Me H H Me CH₂Ph(2-OMe) 89-92 A-355 O Me H H Cl Me H H Me

73-76

TABLE 10 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-356 O Me H H Cl Me H H Me CH₂Ph(2-CN) 107-110 A-357 O Me H H Cl Me H HMe CH₂Ph(3-CN) 95-98 A-358 O Me H H Me Me H H Me CH₂Ph(2-Cl) 107-110A-359 O Me H H Cl H H H Pr-c CH₂Ph(2-Me) 94-97 A-360 O Me H H Me H H HMe CH₂Ph(2-CN) 63-66 A-361 O Me CH₂Ph(2-CN) H Me H H H Me CH₂Ph(2-CN)1.5761 A-362 O Me H H Me H H H Me CH₂Ph(3-Me) 69-72 A-363 O Me H H Me HH H Me CH₂Ph(4-Me) 92-95 A-364 O Me H H Me H H H Me CH₂Ph(3-Cl) 68-70A-365 O Me H H Me H H H Me CH₂Ph(4-Cl) 86-89 A-366 O Me CH₂Ph(4-Cl) H MeH H H Me CH₂Ph(4-Cl) 1.5778 A-367 O Me H H Cl Me H H Me CH₂Ph(2-F) 85-88A-368 O Me H H Me H H H Me CH₂C(Me)═NOMe 1.5362 A-369 O Me H H Me H H HMe CH₂CH₂Ph 1.5661 A-370 O Me H H Cl H H H Me

76-81 A-371 O Me H H F H H H Me CH₂Ph(3-Cl) 48-51 A-372 O Me H H F H H HMe CH₂Ph(4-Cl) 85-88 A-373 O Me H H F H H H Me CH₂Ph(3-Me) 1.5601 A-374O Me H H F H H H Me CH₂Ph(4-Me) 84-87 A-375 O Me H H F H H H MeCH₂Ph(3-CF₃) 50-52 A-376 O Me H H F H H H Me CH₂Ph(4-CF₃) 79-82 A-377 OMe H H F H H H Me CH₂Ph(2-CN) 87-90 A-378 O Me H H F H H H MeCH(Me)Ph(2-Cl) 1.5621 A-379 O Me H H F H H H Me CH(Me)Ph(3-Cl) 1.5599A-380 O Me H H F H H H Me CH(Me)Ph(4-Cl) 85-88 A-381 O Me H H Me Me MeMe Me CH₂Ph A-382 O Me H H Cl Cl Cl Cl Me CH₂Ph A-383 O Me H H Cl H H HPr-c CH₂Ph 1.5731 A-384 O Me H H Cl Me H H Me CH₂Ph(4-CN) 120-122 A-385O Me H H H H H H Me Ph(2-CN,3-Cl) A-386 O Me H H H H H H MeCH₂Ph(2,3-(Cl)₂) 71-74 A-387 O Me H H H H H H Me CH₂Ph(2,4-(Cl)₂) 96-99A-388 O Me H H H H H H Me CH₂Ph(2,5-(Cl)₂) 94-97 A-389 O Me H H H H H HMe CH₂Ph(2,6-(Cl)₂) 92-95 A-390 O Me H H H H H H Me CH₂Ph(3,4-(Cl)₂)56-59 A-391 O Me H H H H H H Me CH₂Ph(3,5-(Cl)₂) 76-78 A-392 O Me H H HH H H Me Ph(3,4,6-Cl₂) A-393 O Me H H H H H H Me Ph(3-Cl,5-OH) A-394 OMe H H Cl H H H Me CH₂COPh 1.5768 A-395 O Me H H Cl H H H Me

147-150 A-396 O Me H H Cl H H H Me

A-397 O Me H H Cl H H H Me

TABLE 11 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-398 O Me H H H H H H Me CH₂Ph(2-F) 1.5657 A-399 O Me H H H H H H MeCH₂Ph(3-F) 1.5641 A-400 O Me H H H H H H Me CH₂Ph(4-F) 88-91 A-401 O MeH H Cl H H H Me CH₂COPh(4-Me) 90-93 A-402 O Me H H Cl H H H Me

 99-102 A-403 O Me H H Cl H H H Me CH₂COPh(4-Cl)  99-102 A-404 O Me H HCl H H H Me CH₂COPh(4-OMe) 63-66 A-405 O Me H H Cl H H H Pr-c

1.5687 A-406 O Me H H Cl H H H Me CH(Me)Ph(2-Me) 1.5719 A-407 O Me H HCl H H H Me CH(Me)Ph(3-Me) 1.5702 A-408 O Me H H Cl H H H MeCH(Me)Ph(4-Me) 1.5693 A-409 O Me H H Cl H H H Me

 98-101 A-410 O Me H H Cl H H H Me

A-411 O Me H H Cl H H H Me

A-412 O Me H H Cl H H H Me CH(C(Me)═NOMe)₂ 1.5411 A-413 O Me H H Cl H HH Me

123-126 A-414 O Me H H Cl H H H Me CH₂Ph(2-NO₂) 104-107 A-415 O Me H HCl H H H Me

74-77 A-416 O Me H H Cl H H H Me

76-79 A-417 O Me H H Cl H H H Me

93-95 A-418 O Me H H Cl H H H Me

56-59 A-419 O Me H H Cl H H H Me

68-71 A-420 O Me H H H H H H Me

1.5731 A-421 O Me H H Cl H H H Me

116-119

TABLE 12 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-422 O Me H H Cl H H H Me

83-86 A-423 O Me H H Cl H H H Me

103-105 A-424 O Me H H Cl H H H Me

A-425 O Me H H Cl H H H Me

A-426 O Me H H Cl H H H Me

64-67 A-427 O Me H H F H H H Me CH₂Ph(3-OCF₃) 35-37 A-428 O Me H H F H HH Me CH₂Ph(3-CN) 1.5666 A-429 O Me H H Cl Me H H Me

1.5769 A-430 O Me H H F H H H Me

1.5609 A-431 O Me H H Cl H H H Me

 97-100 A-432 O Me H H Cl H H H Me

93-96 A-433 O Me H H Cl H H H Me

141-144 A-434 O Me H H Me H H H Me

72-75 A-435 O Me Me H Cl Me H H Me CH₂Ph(2-Cl) 1.5714 A-436 O Me H H ClH H H H CH₂Ph(2-Cl) 89-91 A-437 O Me H H Cl H H H H CH₂Ph(3-Cl) 90-93A-438 O Me H H Cl H H H H CH₂Ph(4-Cl) 137-140 A-439 O Me H H Cl H H H H

1.5839 A-440 O Me H H F H H H Me

1.6004 A-441 O Me H H Cl Me H H Me

111-114 A-442 O Me H H Cl Me H H Me CH₂Ph(2-Cl) 88-91

TABLE 13 m.p.(° C.) Comp. or No. G R¹ R² R³ X¹ X² X³ X⁴ Q Y RI(n_(D) ²⁰)A-443 O Me H H Cl H H H Me

1.5549 A-444 O Me H H Cl H H H Me

A-445 O Me H H Cl H H H Me

1.5825 A-446 O Me H H Cl H H H Me

A-447 O Me H H Cl H H H Me

1.5689 A-448 O Me H H Cl H H H Me

94-97 A-449 O Me H H Cl H H H Me

111-114 A-450 O Me H H Cl H H H Me

1.5649

Typical processes for producing the carbamate derivative represented bythe general formula [I] as the compound of the present invention, willbe exemplified below. Here, the novel compound represented by thegeneral formula [I] has a C═N double bond and thereby may form as an E/Zisomer mixture in some cases. The isomer mixture can be isolated intoindividual component by a purification method such as crystallization orcolumn chromatography. An individual isomer and a mixture thereof areincluded in the present invention.

(wherein each of G, R¹, R², R³, Q, X, Y and n is as defined above.)

The compound [I] of the present invention can be produced by reacting acompound [II] and a compound [III] in an inert solvent (see Jikkenkagaku Kouza (Experimental Chemical Lecture), fourth edition, vol. 20,p. 349-355 (The Chemical Society of Japan) for example). Here, thematerial compound [III] to be used in the present production process mayform a salt with e.g. hydrochloric acid or sulfuric acid. The compound[III] may be produced in accordance with a known process (see Jikkenkagaku Kouza, fourth edition, vol. 20, p. 342-349 for example).

With respect to the amount of the material compound to be used in thepresent reaction, the compound [III] is properly selected within a rangeof from 1 to 50 equivalents based on the compound [II], preferably from1 to 10 equivalents. The inert solvent which can be used in the presentproduction process may, for example, be an alcohol such as methanol,ethanol, propanol or isopropanol, an ether such as diethyl ether,diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane ordiethylene glycol dimethyl ether, an aromatic hydrocarbon such asbenzene, chlorobenzene, nitrobenzene or toluene, or water. These inertsolvents may be used alone or as mixed.

In the present production process, an acid such as hydrochloric acid oracetic acid, or a base such as sodium acetate, sodium carbonate orsodium hydrogencarbonate, may coexist, and they may be used alone or incombination. The amount is properly selected within a range of from0.001 to 50 equivalents based on the compound [II], preferably from 0.01to 10 equivalents. The reaction temperature is within a range of from−10° C. to the boiling point of the inert solvent to be used, andpreferably within a range of from 0° C. to the boiling point of theinert solvent to be used. The reaction time varies depending upon e.g.the reaction temperature and the reaction amount, but may be selectedwithin a range of from 1 to 48 hours in general. After completion of thereaction, the desired product is isolated from the reaction system by aconventional method and may be purified by e.g. column chromatography orrecrystallization, as the case requires.

(wherein each of G, R¹, R², R³, X and n is as defined above, Q′ is acyano group or a nitro group, and A is a C₁-C₁₀ alkyl group.)

A compound [I-a] of the present invention can be produced by reacting acompound [IV] and a nitrite ester [V] in the presence of a base (seeOrganic Syntheses, vol. 6, p.199 (1988) for example). With respect tothe amount of the material compound to be used in the present reaction,the compound [V] is properly selected within a range of from 1 to 50equivalents based on the compound [IV], preferably from 1 to 10equivalents.

The base to be used in the present production process may, for example,be an alkali metal alcoholate such as sodium methoxide, sodium ethoxideor potassium tert-butoxide, or an inorganic base such as sodiumhydroxide, potassium hydroxide, sodium carbonate or potassium carbonate,and the amount of the base is properly selected within a range of from0.5 to 50 equivalents based on the compound [IV], preferably from 1 to10 equivalents.

The inert solvent which can be used in the present production processmay be one which does not inhibit the progress of the present productionprocess, and an ether such as diethyl ether, diisopropyl ether,tetrahydrofuran, dioxane, 1,2-dimethoxyethane or diethylene glycoldimethyl ether, a halogenated hydrocarbon such as dichloromethane,chloroform, carbon tetrachloride or tetrachloroethane, an aromatichydrocarbon such as benzene, chlorobenzene or toluene, or an alcoholsuch as methanol, ethanol, propanol or isopropanol, may, for example, beused. These inert solvents may be used alone or as mixed.

The reaction temperature is within a range of from −70° C. to theboiling point of the inert solvent to be used, and preferably from −20°C. to the boiling point of the inert solvent to be used. The reactiontime varies depending upon e.g. the reaction temperature and thereaction amount, but may be selected within a range of from 1 to 100hours in general, preferably from 12 to 75 hours.

After completion of the reaction, the desired product is isolated fromreaction system by a conventional method and may be purified by e.g.column chromatography or recrystallization, as the case requires.

(wherein each of G, R¹, R², R³, X, Q and n is as defined above, Y′ hasthe same meaning as the above-mentioned Y except for hydrogen, and L isa leaving group and is a halogen atom or a sulfonate such as tosyloxy ormesyloxy.)

A compound [I-e] of the present invention can be produced by reacting acompound [I-b] of the present invention and a compound [VI] in thepresence of a base.

With respect to the amount of the material compound to be used in thepresent reaction, the compound [VI] is properly selected within a rangeof from 1 to 50 equivalents based on the compound [I-b], preferably from1 to 5 equivalents.

An inert solvent may be used in the present production process in somecases. The inert solvent may be one which does not inhibit the progressof the present reaction, and a ketone such as acetone, methyl ethylketone or cyclohexanone, an ether such as diethyl ether, diisopropylether, tetrahydrofuran, dioxane, dimethoxyethane or diethylene glycoldimethyl ether, an ester such as ethyl acetate or methyl acetate, ahalogenated hydrocarbon such as dichloromethane, chloroform or carbontetrachloride, an aromatic hydrocarbon such as benzene, chlorobenzene,nitrobenzene or toluene, a nitrile such as acetonitrile, orN,N-dimethylformamide, N,N-dimethylacetamide,1,3-dimethyl-2-imidazolinone or dimethylsulfoxide may, for example, beused. These inert solvents may be used alone or as mixed.

As the base which can be used, an alkali metal hydride such as sodiumhydride, an alkali metal alcoholate such as potassium tert-butoxide, oran inorganic salt such as sodium carbonate or potassium carbonate may,for example, be used. The amount of the base may properly be selectedwithin a range of from 1 to 50 equivalents based on the compound [I-b],preferably from 1 to 10 equivalents.

The reaction temperature is within a range of from −70° C. to theboiling point of the inert solvent to be used, preferably within a rangeof from 0° C. to the boiling point of the inert solvent to be used. Thereaction time varies depending upon e.g. the reaction temperature andthe reaction amount, but may be selected within a range of from 1 hourto 72 hours in general. After completion of the reaction, the desiredproduct is isolated from the reaction system by a conventional methodand may be purified by e.g. column chromatography or recrystallization,as the case requires.

{wherein each of G, Q, R¹, R², R³, X, Y and n is as defined above, andL′ is a halogen atom.}

A compound [VIII] can be produced by halogenating a compound [VII] by aknown process (see Jikken kagaku Kouza fourth edition, vol. 19, p.416-482 (The Chemical Society of Japan) for example) (Step 4.1). Acompound [I-c] of the present invention can be produced by reacting thecompound [VIII] with a compound [IX] in the presence of a base in aninert solvent (Step 4.2). Further, a compound [I-d] of the presentinvention can be produced by reacting the compound [VIII] with an alkalimetal cyanate salt and a compound [X] in an inert solvent (see Journalof the Chemical Society of Japan, vol. 87, No. 5, p. 486 (1966) forexample) (Step 4.3).

The halogenating agent which can be used in Step 4.1 of the presentproduction process may, for example, be N-bromosuccinimide,N-chlorosuccinimide or trichloroisocyanuric acid. The amount of thehalogenating agent is properly selected within a range of from 0.5 to 10equivalents based on the compound [VII], preferably from 1 to 3equivalents. A catalyst such as azobisisobutyronitrile or benzoylperoxide may be used in the present step, and its amount is properlyselected within a range of from 0.001 to 10 equivalents based on thecompound [VII], preferably from 0.001 to 1 equivalents.

The inert solvent may be one which does not inhibit the progress of Step4.1, and a halogenated hydrocarbon such as dichloromethane, chloroformor carbon tetrachloride or an aromatic hydrocarbon such as benzene orchlorobenzene may, for example, be used.

The reaction temperature is within a range of from 0° C. to the boilingpoint of the inert solvent to be used. The reaction time variesdepending upon e.g. the reaction temperature and the reaction amount,but may be selected within a range of from several minutes to 48 hoursin general. After completion of the reaction, the desired product isisolated from the reaction system by a conventional method and may bepurified by e.g. column chromatography or recrystallization, as the caserequires.

With respect to the amount of the material compound [IX] to be used inStep 4.2 of the present production process, it is properly selectedwithin a range of from 1 to 50 equivalents based on the compound [VIII],preferably from 1 to 10 equivalents.

As the base to be used, an inorganic salt such as sodium carbonate,potassium carbonate or sodium hydrogencarbonate or an alkali metalhydride such as sodium hydride may be used, and the amount of the baseis properly selected within a range of from 0.5 to 100 equivalents basedon the compound [VIII], preferably from 1 to 10 equivalents.

The inert solvent which can be used may be one which does not inhibitthe progress of Step 4.2, and a ketone such as acetone, methyl ethylketone or cyclohexanone, an ether such as diethyl ether, diisopropylether, tetrahydrofuran, dioxane, monoglyme or diglyme, an ester such asethyl acetate or methyl acetate, a halogenated hydrocarbon such asdichloromethane, chloroform or carbon tetrachloride, an aromatichydrocarbon such as benzene, chlorobenzene, nitrobenzene or toluene, anitrile such as acetonitrile, an alcohol such as methanol, ethanol orbutanol, or N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl2-imidazolinone or dimethylsulfoxide may, for example, be used, andthese inert solvents may be used alone or as mixed.

The reaction temperature is within a range of from −70° C. to theboiling point of the inert solvent to be used, and preferably from −10°C. to the boiling point of the inert solvent to be used. The reactiontime varies depending upon e.g. the reaction temperature and thereaction amount, but may be selected within a range of from severalminutes to 48 hours in general. After completion of the reaction, thedesired product is isolated from the reaction system by a conventionalmethod and may be purified by e.g. column chromatography orrecrystallization, as the case requires.

The alkali metal cyanate salt which can be used in Step 4.3 of thepresent production process may, for example, be potassium cyanate orsodium cyanate. The amount of the metal cyanate salt to be used isproperly selected within a range of from 1 to 50 equivalents based onthe compound [VIII], preferably from 1 to 10 equivalents, and thecompound [X] is properly selected within a range of from 1 to 100equivalents based on the compound [VIII], preferably from 1 to 20equivalents. The inert solvent which can be used may be one which doesnot inhibit the progress of Step 4.3, and a ketone such as acetone,methyl ethyl ketone or cyclohexanone, an ether such as diethyl ether,diisopropyl ether, tetrahydrofuran, dioxane, monoglyme or diglyme, anester such as ethyl acetate or methyl acetate, a halogenated hydrocarbonsuch as dichloromethane, chloroform or carbon tetrachloride, an aromatichydrocarbon such as benzene, chlorobenzene, nitrobenzene or toluene, anitrile such as acetonitrile, an alcohol such as methanol, ethanol orbutanol, or N,N-dimethylformamide, N,N-dimethylacetamide,1,3-dimethyl-2-imidazolinone or dimethylsulfoxide may, for example, beused, and these inert solvents may be used alone or as mixed.

The reaction temperature is within a range of from 0° C. to the boilingpoint of the inert solvent to be used. The reaction time variesdepending upon e.g. the reaction temperature and the reaction amount,but may be selected within a range of form 1 hour to 48 hours ingeneral. After completion of the reaction, the desired product isisolated from the reaction system by a conventional method and may bepurified by e.g. column chromatography or recrystallization, as the caserequires.

{wherein each of G, R¹ and R³ is as defined above, each of X¹, X², X³and X⁴ is a hydrogen atom, a halogen atom, a C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a C₁-C₆ haloalkyl group or a C₁-C₆ haloalkoxy group, Q″ isa hydrogen atom, a haloalkyl group, a C₁-C₆ alkyl group, a C₃-C₆cycloalkyl group or a phenyl group (said group may be substituted by atleast one halogen atom, cyano group, nitro group, C₁-C₄ alkyl group,C₂-C₄ alkenyl group, C₂-C₄ alkynyl group, hydroxyl group, C₁-C₄ alkoxygroup, C₁-C₄ haloalkyl group, C₁-C₄ haloalkoxy group, C₁-C₄alkylcarbonyl group or C₁-C₄ alkoxycarbonyl group).}

A compound [I-f] of the present invention can be produced by diazotizinga compound [XVIII] by sodium nitrite in the presence of e.g.hydrochloric acid in accordance with a known process, and reacting acompound [XIX] therewith in the presence of e.g. sodium acetate andcopper sulfate (see Organic Syntheses vol. 5, p. 139 (1973) forexample).

With respect to the amount of the material compound to be used in thepresent reaction, the compound [XIX] is properly selected within a rangeof from 1 to 50 equivalents based on the compound [XVIII], preferablyfrom 1 to 5 equivalents.

The solvent which can be used in the present production process may beone which does not inhibit the progress of the present reaction. Forexample, an ether such as diethyl ether, diisopropyl ether,tetrahydrofuran, dioxane, dimethoxyethane or diethylene glycol dimethylether, an ester such as ethyl acetate or methyl acetate, a halogenatedhydrocarbon such as dichloromethane, chloroform or carbon tetrachloride,an aromatic hydrocarbon such as benzene, chlorobenzene, nitrobenzene ortoluene, an organic acid such as acetic acid or trifluoroacetic acid, orwater may, for example, be used, and these solvents may be used alone oras mixed.

As the acid to be used in Step 1) diazotization of the presentproduction process, a strong acid such as sulfuric acid,tetrafluoroboric acid, hydrobromic acid or trifluoroacetic acid may beused instead of the above-mentioned hydrochloric acid. The amount isproperly selected within a range of from 1 to 50 equivalents based onthe compound [XVIII], preferably from 2 to 4 equivalents. Further, anitrite ester such as isoamyl nitrite or methyl nitrite may be usedinstead of the above-mentioned sodium nitrite. The amount is properlyselected within a range of from 1 to 50 equivalents based on thecompound [XVIII], preferably from 1 to 2 equivalents. The reactiontemperature is within a range of from −20° C. to 30° C., preferablywithin a range of from −5° C. to 5° C. The reaction time variesdepending upon e.g. the reaction temperature and the reaction amount,but may be selected within a range of from 30 minutes to 2 hours ingeneral. As the copper compound to be used in Step 2) of coupling in thepresent reaction, a copper salt such as copper(I) chloride or copper(II)acetate may be used instead of the above-mentioned copper sulfate. Theamount is properly selected within a range of from 0.02 to 2 equivalentsbased on the compound [XVIII], preferably from 0.02 to 0.5 equivalent.Further, the amount of sodium acetate is properly selected within arange of from 1 to 50 equivalents based on the compound [XVIII],preferably from 4 to 10 equivalents. The reaction temperature is withina range of from −20° C. to 30° C., preferably within a range of from −5°C. to 25° C. The reaction time varies depending upon e.g. the reactiontemperature and the reaction amount, but may be selected within a rangeof from 30 minutes to 2 hours in general. After completion of thereaction, the desired product is isolated from the reaction system by aconventional method and may be purified by e.g. column chromatography orrecrystallization, as the case requires.

The compound [II] as an intermediate for the compound [I] of the presentinvention can be produced, for example, in accordance with the followingknown process, but the process is not limited thereto.

{wherein each of L′, G, Q, R¹, R², R³, X and n is as defined above.}

A compound [XII] can be produced by halogenating a compound [XI] (seeJikken kagaku Kouza fourth edition, vol. 19, p. 416-482 (The ChemicalSociety of Japan) for example) (Step A-1). Further, the intermediate[II] can be produced by reacting the compound [XII] with the compound[IX] in the presence of a base (e.g. an inorganic salt such as sodiumcarbonate, potassium carbonate or sodium hydrogencarbonate or an alkalimetal hydride such as sodium hydride) (Step A-2). Further, anintermediate [II-a] can be produced by reacting the compound [XII] withan alkali metal cyanate salt and the compound [X] in the presence of aninert solvent (see Journal of the Chemical Society of Japan, vol. 87,No. 5, p. 486 (1966) for example) (Step A-3).

The compounds [II] and [IV-a] as intermediates for the compound [I] ofthe present invention can be produced, for example, in accordance withthe following known process, but the process is not limited thereto.

{wherein each of G, Q, R¹, R², R³, X, L′ and n is as defined above, andT is a C₁-C₆ alkyl group.}

A compound [XIV] can be produced by halogenating a compound [XIII] (seeJikken kagaku Kouza, fourth edition, vol. 19, p. 416-482 (The ChemicalSociety of Japan) for example) (Step B-1). A compound [XV] can beproduced by reacting the compound [XIV] with the compound [X] and analkali metal cyanate salt (see Journal of the Chemical Society of Japan,vol. 87, No. 5, p. 486 (1966) for example) (Step B-2). Otherwise, thecompound [XV] can be produced by reacting the compound [XIV] with thecompound [IX] in the presence of an inorganic salt such as sodiumcarbonate, potassium carbonate or sodium hydrogencarbonate or a basesuch as an alkali metal hydride such as sodium hydride (Step B-3). Acompound [XVI] can be produced by reducing the compound [XV] inaccordance with a known process (Jikken kagaku Kouza, fourth edition,vol. 26, p. 159-266 (The Chemical Society of Japan) for example) (B-4).A compound [II-b] can be produced by oxidizing the compound [XVI] inaccordance with a known process (see Jikken kagaku Kouza, fourthedition, vol. 21, p. 2-23 (The Chemical Society of Japan) for example)(Step B-5). A compound [XVII] can be produced by halogenating thecompound [XVI] in accordance with a known process (see Jikken kagakuKouza, fourth edition, vol. 19, p. 416-482 (The Chemical Society ofJapan) for example) (Step B-6).

A compound [IV-a] can be produced by cyanating the compound [XVII] inaccordance with a known process (see Jikken kagaku Kouza, fourthedition, vol. 20, p. 437-462 (The Chemical Society of Japan) forexample) (Step B-7).

The compound [VII] as an intermediate for the compound [I] of thepresent invention can be produced, for example, in accordance with thefollowing known process, but the process is not limited thereto.

(wherein each of R³, Q, X, Y and n is as defined above.)

The compound [VII] of the present invention can be produced by reactingthe compound [XI] and the compound [III] (see Jikken kagaku Kouza,fourth edition, vol. 20, p. 349-355 (The Chemical Society of Japan) forexample). Here, the material compound [III] to be used in the presentproduction process may form a salt with e.g. hydrochloric acid orsulfuric acid.

The compound [XVIII] as an intermediate for the compound [I] of thepresent invention can be produced, for example, in accordance with thefollowing known process, but the process is not limited thereto.

{wherein each of G, R¹, R³, L′, X¹, X², X³ and X⁴ is as defined above.}

An intermediate [XXI] can be produced by reacting a compound [XX] withan alkali metal cyanate salt and the compound [X] in an inert solvent(see Journal of the Chemical Society of Japan, vol. 87, No. 5, p. 486(1966) for example) (Step C-1). An intermediate [XXII] can be producedby nitrating the compound [XXI] with e.g. nitric acid, acetyl nitrate orsodium nitrate (see Jikken kagaku Kouza, fourth edition, vol. 20, p.394-399 (The Chemical Society of Japan) for example) (Step C-2). Theintermediate [XVIII] can be produced by reducing the compound [XXII] inaccordance with a known process (see Jikken kagaku Kouza, fourthedition, vol. 26, p. 159-266 (The Chemical Society of Japan) forexample) (Step C-3).

EXAMPLES

Now, the processes for producing the compound of the present invention,formulation methods and applications will be specifically described withreference to Examples.

Symbols to be used in the text have the following meanings.

¹H-NMR: Proton nuclear magnetic resonance; CDCl₃: Deuterated chloroform;TMS: Tetramethylsilane; s: singlet, d: doublet, t: triplet, q: quartet,quint: quintet, m: multiplet, br: broad, dd: double doublet

Preparation Example 1 Preparation of2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrile(Compound No. A-2)

0.15 g of sodium hydroxide and 0.60 g of methylN-(2-chloro-5-cyanomethylbenzyl)carbamate were added to 5 ml of ethanol,and 0.40 g of t-butyl nitrite was added to the mixture at roomtemperature, followed by stirring for 72 hours. After completion of thereaction, the reaction solution was poured into water, extraction withethyl acetate was carried out, followed by washing with water, and theorganic layer was dried over anhydrous magnesium sulfate. The solventwas distilled off under reduced pressure, and the residue was purifiedby silica gel column chromatography (Wakogel C-200, eluent: hexane/ethylacetate=3/1) to obtain 0.46 g of2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrileas a colorless viscous liquid.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 3.72 (s, 3H); 4.48 (d, 2H); 5.43 (br, 1H);7.43-8.21 (m, 3H); 10.51, 11.15 (br, 1H).

Preparation Example 2 Preparation of2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-methoxyiminoacetonitrile(Compound No. A-3)

0.36 g of2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrileand 0.54 g of a 28% sodium methylate methanol solution were added to 5ml of methanol, and 0.49 g of methyl iodide was added thereto, followedby stirring at room temperature for 24 hours. The reaction solution wasvacuum concentrated, the solvent was distilled off, water was added tothe residue, extraction with ethyl acetate was carried out, and theorganic layer was dried over anhydrous magnesium sulfate. The solventwas distilled off under reduced pressure, and the residue was purifiedby silica gel column chromatography (Wakogel C-200, eluent: hexane/ethylacetate=4/1-5/1) to obtain 0.18 g of2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-methoxyiminoacetonitrileas colorless crystals (m.p. 104-107° C.)

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 3.71 (s, 3H); 4.22 (s, 3H); 4.48 (d, 2H);5.23 (br, 1H); 7.43-8.05 (m, 3H).

Preparation Example 3 Preparation of MethylN-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate (Compound No. A-45)

5.0 g of methyl N-(2-chloro-5-acetylbenzyl)carbamate was dissolved in 10ml of ethanol, and 1.5 g of hydroxylamine hydrochloride, 3.0 g of sodiumacetate and 5 ml of water were added thereto, followed by reflux underheating for 4 hours. After completion of the reaction, water was addedto the reaction mixture, extraction with ethyl acetate was carried out,the organic layer was dried over anhydrous magnesium sulfate, and thesolvent was distilled off under reduced pressure. The obtained crystalswere washed with hexane to obtain 5.2 g of methylN-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate as colorlesscrystals (m.p. 124-127° C.).

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.25 (s, 3H); 3.70 (s, 3H); 4.46 (d, 2H);5.31 (br, 1H); 7.27-7.63 (m, 3H).

Preparation Example 4 Preparation of MethylN-[3-(1-methoxyiminoethyl)benzyl]carbamate (Compound No. A-40)

0.40 g of methyl N-(3-acetylbenzyl)carbamate was dissolved in 10 ml ofethanol, and 0.36 g of methoxyamine hydrochloride and 5 ml of an aqueoussolution of 0.54 g of sodium acetate were added thereto, followed byreflux under heating for 8 hours. After completion of the reaction,water was added to the reaction mixture, extraction with ethyl acetatewas carried out, the organic layer was dried over anhydrous magnesiumsulfate, and the solvent was distilled off under reduced pressure. Theobtained crystals were washed with hexane to obtain 0.40 g of methylN-[3-(1-methoxyiminoethyl)benzyl]carbamate as a pale yellow oilysubstance.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.22 (s, 3H); 3.69 (s, 3H); 3.99 (s, 3H);4.37 (d, 2H); 5.12 (br, 1H); 7.27-7.56 (m, 4H).

Preparation Example 5 Preparation of MethylN-{2-chloro-5-[1-(4-fluorobenzyloxyimino)ethyl]benzyl}carbamate(Compound No. A-83)

0.70 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate wasdissolved in 10 ml of N,N-dimethylformamide, and 0.13 g of 60% sodiumhydride was added thereto under cooling with ice, followed by stirringfor 1 hour. 0.57 g of 4-fluorobenzyl bromide was dissolved in 2 ml ofN,N-dimethylformamide, which was dropwise added to the reaction mixtureunder cooling with ice. After completion of the dropwise addition, themixture was stirred at room temperature for 16 hours. After completionof the reaction, the reaction solution was poured into water, extractionwith ethyl acetate was carried out, followed by washing with water, andthe organic layer was dried over anhydrous magnesium sulfate. Thesolvent was distilled off under reduced pressure, and the residue waspurified by silica gel column chromatography (Wakogel C-200, eluent:hexane/ethyl acetate=5/1) to obtain 0.75 g of methylN-{2-chloro-5-[1-(4-fluorobenzyloxyimino)ethyl]benzyl}carbamate (m.p.101-103° C.) as colorless crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.22 (s, 3H); 3.69 (s, 3H); 4.45 (d, 2H);5.10 (br, 1H); 5.18 (s, 2H); 7.02-7.65 (m, 7H).

Preparation Example 6 Preparation of MethylN-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate (Compound No. A-45)

10.7 g of methyl N-[5-amino-2-chlorobenzyl]carbamate was dissolved in 33g of 14% hydrochloric acid, followed by stirring at room temperature for1 hour. 7 ml of an aqueous solution of 3.8 g of sodium nitrite wasdropwise added to the solution with stirring at from 0 to 5° C. Theformed diazonium salt was dropwise added to a mixed solvent ofwater/ethyl acetate/toluene (80 ml/40 ml/40 ml) of 21.7 g of sodiumacetate, 2.6 g of copper sulfate and 5.9 g of acetaldoxime withvigorously stirring at from 0 to 5° C. over a period of 15 minutes,followed by stirring at room temperature further for 2 hours. Thereaction solution was acidified with hydrochloric acid, extraction withethyl acetate was carried out, followed by washing with water, and theorganic layer was dried over anhydrous magnesium sulfate. The solventwas distilled off under reduced pressure, the obtained crude crystalswere washed with a mixed solvent of ether/ethyl acetate to obtain 2.8 gof methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate ascolorless crystals (m.p. 124-127° C.).

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.25 (s, 3H); 3.70 (s, 3H); 4.46 (d, 2H);5.31 (br, 1H); 7.27-7.63 (m, 3H).

Preparation Example 7 Preparation of MethylN-{2-methyl-5-[1-(6-methylpyridin-2-ylmethoxy)iminoethyl]benzyl}carbamate (Compound No. A-434)

0.43 g of methyl N-[2-methyl-5-(1-hydroxyiminoethyl)benzyl]carbamate wasdissolved in 15 ml of N,N-dimethylformamide, 0.75 g of potassiumcarbonate and 0.32 g of 2-chloro-6-methylpyridine hydrochloride wereadded thereto, followed by stirring under heating at from 90 to 100° C.for 8 hours. After completion of the reaction, the reaction solution waspoured into water, extraction with ethyl acetate was carried out,followed by washing with water, and the organic layer was dried overanhydrous magnesium sulfate. The solvent was distilled off under reducedpressure, and the residue was purified by silica gel columnchromatography (Wakogel C-200, eluent: hexane/ethyl acetate=4/1) toobtain 0.30 g of methyl N-{2-methyl-5-[1-(6-methylpyridin-2-ylmethoxy)iminoethyl]benzyl}carbamate (m.p. 72-75° C.) as pale yellowcrystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.30 (s, 3H); 2.32 (s, 3H); 2.56 (s, 3H);3.69 (s, 3H); 4.35 (d, 2H); 4.94 (br, 1H); 5.33 (s, 2H); 7.04-7.59 (m,6H).

Now, ¹H-NMR(CDCl₃/TMS, δ (ppm)) data of some among examples of thecompound of the present invention, will be shown in Tables 14 to 20.

TABLE 14 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-2 3.72(s,3H); 4.48(d, 2H); 5.43(br, 1H); 7.43-8.21(m, 3H) A-37 2.20, 2.25(s, 3H);3.70(s, 3H); 4.37(d, 2H); 4.54, 4.71(d, 2H); 5.08(br, 1H); 5.20-5.38(m,2H); 6.00-6.11(m, 1H); 7.29-7.56(m, 4H) A-38 2.17, 2.25(s, 3H); 3.68(s,3H); 4.35(d, 2H); 5.05(br, 1H); 5.09, 5.24(s, 2H); 7.28-7.55(m, 9H) A-391.24, 1.33(t, 3H); 2.18, 2.22(s, 3H); 3.69(s, 3H); 4.09, 4.24(q, 2H);4.37(d, 2H); 5.14(br, 1H); 7.26-7.56(m, 4H) A-40 2.22(s, 3H); 3.69(s,3H); 3.99(s, 3H); 4.37(d, 2H); 5.12(br, 1H); 7.27-7.56(m, 4H) A-413.67(s, 3H); 4.35(dd, 2H); 4.66-4.69(m, 2H); 5.17(br, 1H); 5.95-6.08(m,2H); 7.25-7.48(m, 9H) A-42 3.67(s, 3H); 3.96(s, 3H); 4.11(dd, 2H);5.30(br, 1H); 7.25-7.80(m, 9H) A-43 1.27, 1.29(t, 3H); 3.67(s, 3H);4.22, 4.23(q, 2H); 4.34(dd, 2H); 5.15(br, 1H); 7.27-7.48(9H) A-500.98(t, 3H); 1.75(quint, 2H); 2.21(s, 3H); 3.69(s, 3H); 4.15(t, 2H);4.46(d, 2H); 5.19(br, 1H); 7.34(d, 1H); 7.51(d, 1H); 7.66(s, 1H) A-511.30(d, 6H); 2.19(s, 3H); 3.69(s, 3H); 4.41-4.49(m, 3H); 5.20(br, 1H);7.34(d, 1H); 7.52(dd, 1H); 7.65(s, 1H) A-53 0.95(t, 3H); 1.27(d, 3H);1.52-1.78(m, 2H); 2.19(s, 3H); 3.68(s, 3H); 4.21-4.28(m, 1H); 4.44(d,2H); 5.27(br, 1H); 7.30-7.65(m, 3H) A-54 0.96(d, 6H); 2.04(m, 1H);2.21(s, 3H); 3.68(s, 3H); 3.96(d, 2H); 4.45(d, 2H); 5.24(br, 1H);7.33(d, 1H); 7.50(dd, 1H); 7.65(s, 1H) A-55 1.35(t, 9H); 2.18(d, 3H);3.69(s, 3H); 4.45(d, 2H); 5.20(br, 1H); 7.27-7.63(m, 3H)

TABLE 15 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-560.30-0.35(m, 2H); 0.54-0.60(m, 2H); 1.14-1.27(m, 1H); 2.23(s, 3H);3.69(s, 3H); 4.01(d, 2H); 4.45(d, 2H); 5.20(br, 1H); 7.34(d, 1H);7.51(dd, 1H); 7.66(s, 1H) A-62 2.05(quint, 2H); 2.21(s, 3H); 2.74(t,2H); 3.69(s, 3H); 4.22(t, 2H); 4.46(d, 2H); 5.18(br, 1H); 7.17-7.67(m,8H) A-63 1.29(t, 3H); 2.29(s, 3H); 3.69(s, 3H); 4.25(q, 2H); 4.47(d,2H); 4.73(s, 2H); 5.22(br, 1H); 7.34(d, 1H); 7.50(dd, 1H); 7.64(s, 1H)A-64 1.49(s, 9H); 2.28(s, 3H); 3.69(s, 3H); 4.46(d, 2H); 4.63(s, 2H);5.19(br, 1H); 7.35(1H); 7.5(dd, 1H); 7.64(br, 1H) A-91 2.25(s, 3H);2.39(s, 3H); 3.70(s, 3H); 4.45(d, 2H); 5.22(s, 2H); 5.31(br, 1H);7.13-7.54(m, 7H) A-94 2.24(s, 3H); 3.69(s, 3H); 3.82(s, 3H); 4.45(d,2H); 5.19(br, 1H); 5.21(s, 3H); 6.84-7.66(m, 7H) A-95 2.21(s, 3H);3.70(s, 3H); 3.81(s, 3H); 4.45(d, 2H); 5.16(s, 3H); 5.21(br, 1H);6.89-7.66(m, 7H) A-98 1.33, 1.35(s, 9H); 2.23, 2.24(s, 3H); 3.69(s, 3H);4.45(d, 2H); 5.21, 5.23(s, 2H); 5.26(br, 1H); 7.32-7.67(m, 7H) A-1002.25(s, 3H); 3.68(s, 3H); 4.44(d, 2H); 5.22(br, 1H); 5.27(s, 2H);7.32-7.65(m, 7H) A-150 2.23(s, 3H); 2.40(s, 3H); 3.69(s, 3H); 4.46(d,2H); 5.18(br, 1H); 5.24(s, 2H); 7.30-7.49(m, 7H) A-155 2.22(s, 3H);2.36(s, 3H); 2.39(s, 3H); 3.67(s, 3H); 4.44(d, 2H); 5.20(br, 1H);5.21(s, 2H); 7.10-7.48(m, 6H) A-158 2.20(s, 3H); 2.40(s, 3H); 2.39(s,3H); 3.69(s, 3H); 3.81(s, 3H); 4.46(d, 2H); 5.15(br, 1H + s, 2H);6.89-7.49(m, 6H) A-189 1.39, 1.74(d, 3H); 2.21(s, 3H); 3.69(s, 3H);4.46(d, 2H); 4.63, 4.77(d, 2H); 5.14-5.29(br, 1H); 5.67-6.03(m, 2H);7.33-7.65(m, 3H) A-198 2.20(s, 3H); 2.48(q, 2H); 3.69(s, 3H); 4.24(t,2H); 4.46(d, 2H); 5.05-5.16(m, 2H); 5.20(br, 1H); 5.80-5.94(m, 1H);7.33-7.66(m, 3H)

TABLE 16 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-206 2.17(s,3H); 3.68(s, 3H); 4.44(d, 2H); 5.09(s, 2H); 5.23(br, 1H); 7.26-7.53(m,8H) A-207 2.18(s, 3H); 3.68(s, 3H); 4.46(d, 2H); 5.17(br, 1H); 5.20(s,2H); 7.22-7.56(m, 7H) A-215 2.21(s, 3H); 3.69(s, 3H); 4.46(d, 2H);5.17(br, 1H); 5.69(s, 2H); 7.26-8.18(m, 10H) A-216 1.61(d, 3H); 2.26(s,3H); 4.43(d, 2H); 5.15(br, 1H); 5.37(q, 1H); 7.26-7.60(m, 8H) A-2192.25(br, 3H); 3.75, 3.79(s, 3H); 4.53(br, 4H); 5.47, 5.53(s, 2H);7.19-7.78(m, 1H) A-229 2.20(s, 3H); 2.56(t, 4H); 2.75(t, 2H); 3.69(s,3H); 3.73(t, 4H); 4.34(t, 2H); 4.45(d, 2H); 5.34(br, 1H); 7.28-7.65(m,3H) A-234 2.32(s, 3H); 2.68(t, 2H); 3.68(s, 3H); 4.30(t, 2H); 4.45(d,2H); 5.40(br, 1H); 7.33-7.65(m, 3H) A-240 2.24(s, 3H); 2.68(m, 1H);2.87(m, 1H); 3.32(m, 1H); 3.69(s, 3H); 4.08-4.47(m, 2H); 4.46(d, 2H);5.23(br, 1H); 7.35(d, 1H); 7.51(dd, 1H); 7.66(s, 1H) A-241 2.24(s, 3H);3.69(s, 3H); 3.90-4.05(m, 4H); 4.25(d, 2H); 4.45(d, 2H); 5.25(t, br,2H); 7.34(d, 1H); 7.51(dd, 1H); 7.65(s, 1H) A-251 0.89(t, 3H);1.23-1.41(m, 8H); 1.71(quintet, 2H); 2.19(s, 3H); 3.68(s, 3H); 4.17(q,2H); 4.45(d, 2H); 5.23(br, 1H); 7.34(dd, 1H); 7.51(dd, 1H); 7.65(s, 1H)A-266 2.27(s, 3H); 3.68(s, 3H); 4.44(d, 2H); 5.25(br, 1H); 5.31(s, 2H);7.33-8.27(m, 7H) A-269 2.25(s, 3H); 2.62(s, 3H); 3.69(s, 3H); 4.46(d,2H); 5.22(br, 1H); 5.28(s, 2H); 7.33-8.01(m, 7H) A-273 1.30(d, 6H);3.70(s, 3H); 4.41-4.49(m, 3H); 5.18(br, 1H); 7.35(d, 1H); 7.62(dd, 1H);7.57(s, 1H); 8.00(s, 1H) A-286 2.29(s, 3H); 2.56(s, 3H); 3.67(s, 3H);4.44(d, 2H); 5.33(br, 3H); 7.05(d, 1H); 7.19(d, 3H); 7.32(d, 1H);7.49-7.64(m, 3H)

TABLE 17 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-289 3.17(s,3H); 3.69(s, 3H); 4.48(d, 2H); 5.18(br, 1H); 5.35(s, 2H); 7.27-7.69(m,7H) A-290 3.17(s, 3H); 3.68(s, 3H); 4.49(d, 2H); 5.26(br, 1H); 5.37(s,2H); 7.24-7.77(m, 6H); 8.60(d, 1H) A-291 2.23(s, 3H); 3.69(s, 3H);4.00(s, 3H); 4.45(d, 2H); 5.19(br, 1H); 5.24(s, 2H); 7.33-7.68(m, 7H)A-292 1.18(t, 3H); 2.21(s, 3H); 2.81(q, 2H); 3.69(s, 3H); 4.46(d, 2H);4.67(s, 2H); 5.18(br, 1H); 7.36d, 1H); 7.50(dd, 1H); 7.65(s, 1H) A-2931.09-1.22(m, 3H); 1.92(s, 3H); 2.70-2.79(m, 2H); 3.69(s, 3H); 3.85,3.90(s, 3H); 4.46(d, 2H); 4.68, 4.99(s, 2H); 5.17(br, 1H); 7.34-7.64(m,3H) A-297 1.41(t, 3H); 2.79(q, 2H); 3.68(s, 3H); 4.45(d, 2H); 5.20(br,1H); 5.43(s, 2H); 7.33-7.73(m, 7H) A-298 1.17(t, 3H); 1.43(d, 3H);2.19(s, 3H); 2.80(q, 2H); 3.70(s, 3H); 4.45(d, 2H); 4.65(q, 1H);5.17(br, 1H); 7.35(d, 1H); 7.50(dd, 1H); 7.62(s, 1H) A-299 1.09-1.16(m,3H); 1.38, 1.43(d, 3H); 1.82, 1.83(s, 3H); 2.68, 2.82(m, 2H); 3.69(s,3H); 3.84, 3.88(s, 3H); 4.45(d, 2H); 4.84, 5.64(q, 1H); 5.21(br, 1H);7.34(d, 1H); 7.49(d, 1H); 7.61(s, 1H) A-300 1.09-1.16(m, 3H);1.23-1.29(m, 3H); 1.38, 1.42(d, 3H); 1.83(s, 3H); 2.68-2.82(m, 2H);3.69(s, 3H); 4.03-4.16(m, 2H); 4.45(d, 2H); 4.84, 5.54(q, 1H); 5.21(br,1H); 7.34(dd, 1H); 7.52(dd, 1H); 7.65(s, 1H) A-303 1.11(t, 3H); 2.75(q,2H); 3.69(s, 3H); 4.45(d, 2H); 5.22(br, 3H); 7.28-7.65(m, 8H) A-3041.12(t, 3H); 2.76(q, 2H); 3.69(s, 3H); 3.82(s, 3H); 4.46(d, 2H);5.20(br, 3H); 3.84(dd, 1H); 6.95-6.99(m, 2H); 7.25-7.36(m, 2H); 7.50(dd,1H); 7.65(s, 1H) A-305 1.17(t, 3H); 2.82(q, 2H); 3.68(s, 3H); 4.45(d,2H); 5.18(br, 1H); 5.36(s, 2H); 7.19-7.73(m, 6H); 8.59(d, 1H) A-3091.59(d, 3H); 3.00(s, 3H); 3.68(s, 3H); 4.43(d, 2H); 5.14(br, 1H);5.75(q, 1H); 7.16-7.59(m, 7H) A-310 1.58(d, 3H); 2.25(s, 3H); 3.67(s,3H); 4.42(d, 2H); 5.21(br, 1H); 5.32(q, 1H); 7.24-7.59(m, 7H)

TABLE 18 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-312 1.49,1.60(d, 3H); 2.26(s, 3H); 3.68(s, 3H); 3.81(s, 3H); 4.43(d, 2H);5.15(br, 1H); 5.34(q, 1H); 6.81(dd, 1H); 6.92-6.97(m, 2H); 7.24-7.32(m,2H); 7.48(dd, 1H); 7.60(s, 1H) A-313 1.62(d, 3H); 2.27(s, 3H); 3.68(s,3H); 4.43(d, 3H); 4.43(d, 2H); 5.15(br, 1H); 5.40(q, 1H); 7.30-7.61(m,7H) A-315 2.49(s, 3H); 2.33(s, 3H); 3.70(s, 3H); 3.82(s, 3H); 4.37(d,2H); 4.86(br, 1H); 5.21(s, 2H); 6.83-7.53(m, 7H) A-322 2.23(br, 6H);3.74-3.81(br, 9H); 4.33-4.54(br, 4H); 5.21(s, 2H); 6.68-7.48(m, 11H)A-329 2.25(s, 3H); 3.69(s, 3H); 3.82(s, 3H); 4.41(d, 2H); 5.07(br, 1H);5.20(s, 2H); 6.84-7.63(m, 7H) A-332 2.29(s, 3H); 3.69(s, 3H); 4.46(d,2H); 5.26(br, 1H); 5.37(s, 2H); 7.19-7.73(m, 5H); 8.60(d, 1H) A-3332.31(s, 3H); 2.33(s, 3H); 3.70(s, 3H); 4.37(d, 2H); 4.86(br, 1H);5.36(s, 2H); 7.15-7.72(m, 6H); 8.59(d, 1H) A-338 2.30(s, 3H); 3.71(s,3H); 4.38(d, 2H); 4.99(br, 1H); 5.36(s, 2H); 7.22-7.56(m, 8H) A-3392.27(s, 3H); 3.71(s, 3H); 4.38(d, 2H); 5.00(br, 1H); 5.21(s, 2H);7.26-7.54(m, 8H) A-341 0.60-0.70(m, 2H); 0.93-0.99(m, 2H); 2.19-2.28(m,1H); 3.69(s, 3H); 4.44(d, 2H); 5.14(br, 1H); 5.32(s, 2H); 7.21-7.55(m,7H) A-343 2.25(s, 3H); 2.40(s, 3H); 3.70(s, 3H); 4.37(d, 2H); 5.03(br,1H); 5.26(s, 2H); 7.17-7.56(m, 8H) A-344 2.25(s, 3H); 2.37(s, 3H);3.70(s, 3H); 4.37(d, 2H); 5.04(br, 1H); 5.20(s, 2H); 7.11-7.56(m, 8H)A-348 2.30(s, 3H); 3.69(s, 3H); 4.37(d, 2H); 5.06(br, 1H); 5.45(s, 2H);7.26-7.68(m, 8H) A-349 2.27(s, 3H); 3.69(s, 3H); 4.37(d, 2H); 5.07(br,1H); 5.27(s, 2H); 7.25-7.67(m, 8H)

TABLE 19 Comp. No. ¹H-NMR δ value (ppm) Solvent CDCl₃/TMS A-350 2.27(s,3H); 3.68(s, 3H); 4.35(d, 2H); 5.11(br, 1H); 5.28(s, 2H); 7.25-7.62(m,8H) A-361 2.23, 2.27(s, 6H); 3.79(s, 3H); 4.50-4.75(br, 4H); 5.40(s,2H); 7.11-7.70(m, 11H) A-366 2.21(br, 6H); 3.80(s, 3H); 4.25-4.52(br,4H); 5.18(s, 2H); 7.13-7.45(m, 11H) A-368 1.93(s, 3H); 2.22, 2.24(s,3H); 2.34(s, 3H); 3.70(s, 3H); 3.84, 3.90(s, 3H); 4.33(d, 2H); 4.69,5.00(s, 2H); 4.89(br, 1H); 7.17(d, 1H); 7.46(d, 1H); 7.52(s, 1H) A-3692.19(s, 3H); 2.34(s, 3H); 3.04(t, 2H); 3.70(s, 3H); 4.32-4.41(m, 4H);4.86(br, 1H); 7.16-7.52(m, 8H) A-373 2.22(s, 3H); 2.35(s, 3H); 3.69(s,3H); 4.41(d, 2H); 5.07(br, 1H); 5.18(s, 2H); 6.96-7.63(m, 7H) A-3781.58(d, 3H); 2.30(s, 3H); 3.68(s, 3H); 4.89(d, 2H); 5.05(br, 1H);5.74(q, 1H); 6.96-7.57(m, 7H) A-379 1.58(d, 3H); 2.26(s, 3H); 3.68(s,3H); 4.39(d, 2H); 5.05(br, 1H); 5.31(q, 1H); 6.97-7.57(m, 7H) A-3830.61, 0.92(m, 4H); 2.21(m, 1H); 3.69(s, 3H); 4.44(d, 2H); 5.14(br, 1H);5.21(s, 2H); 7.26-7.47(m, 8H) A-394 2.32(s, 3H); 3.68(s, 3H); 4.44(d,2H); 5.18(br, 1H); 5.42(s, 2H); 7.31-7.98(m, 8H) A-398 2.26(s, 3H);3.70(s, 3H); 4.38(d, 2H); 5.00(br, 1H); 5.31(s, 2H); 7.04-7.56(m, 8H)A-399 2.27(s, 3H); 3.70(s, 3H); 4.38(d, 2H); 5.01(br, 1H); 5.23(s, 2H);6.96-7.55(m, 8H) A-400 1.90(s, 6H); 2.26(s, 3H); 3.68(s, 3H); 3.89(s,6H); 4.43(d, 2H); 5.26(s, 2H); 5.41(br, 1H); 7.32-7.63(m, 3H) A-4050.66, 0.97(m, 4H); 2.28(m, 1H); 3.69(s, 3H); 4.43(d, 2H); 5.16(br, 1H);5.34(s, 2H); 7.18-7.74(m, 6H); 8.58(d, 1H)

TABLE 20 Comp. No. ¹H—NMR δ value (ppm) Solvent CDCl₃/TMS A-406 1.58(d,3H); 2.25(s, 3H); 2.39(s, 3H); 3.69(s, 3H); 4.41(d, 2H); 5.19(br, 1H);5.58(q, 1H); 7.15-7.60(m, 7H) A-407 1.59(d, 3H); 2.25(s, 3H); 2.36(s,3H); 3.68(s, 3H); 4.42(d, 2H); 5.17(br, 1H); 5.33(q, 1H); 7.07-7.60(m,7H) A-408 1.59(d, 3H); 2.24(s, 3H); 2.34(s, 3H); 3.68(s, 3H); 4.43(d,2H); 5.16(br, 1H); 5.33(q, 1H); 7.14-7.60(m, 7H) A-412 1.90(s, 6H);2.26(s, 3H); 3.68(s, 3H); 3.89(s, 6H); 4.43(d, 2H); 5.26(s, 1H);5.41(br, 1H); 7.33(d, 1H); 7.52(dd, 1H); 7.62(d, 1H) A-420 2.32(s, 3H);2.57(s, 3H); 3.70(s, 3H); 4.37(d, 2H); 5.05(br, 1H); 5.34(s, 2H);7.04-7.60(m, 7H) A-428 2.26(s, 3H); 3.68(s, 3H); 4.41(d, 2H); 5.15(br,1H); 5.24(s, 2H); 7.00-8.21(m, 7H) A-429 2.29(s, 3H); 2.38(s, 3H);2.56(s, 3H); 3.67(s, 3H); 4.44(d, 2H); 5.27(br, 1H); 5.33(s, 2H);7.06(d, 1H); 7.19(d, 1H); 7.47(br, 2H); 7.57(t, 1H) A-430 2.30(s, 3H);2.56(s, 3H); 3.68(s, 3H); 4.41(d, 2H); 5.15(br, 1H); 5.32(s, 2H);6.98-7.62(m, 6H) A-435 2.26(s, 3H); 2.40(s, 3H); 2.88, 2.95(br, 3H);3.71, 3.76(br, 3H); 4.63, 4.67(br, 2H); 5.35(s, 2H); 7.22-7.47(m, 6H)A-439 2.57(s, 3H); 3.69(s, 3H); 4.44(d, 2H); 5.30(br, 3H); 7.06-7.61(m,6H); 8.16(s, 1H) A-440 2.31(s, 3H); 3.64(s, 3H); 4.37(d, 2H); 5.37(br,1H); 5.52(s, 2H); 6.94-8.27(m, 9H) A-443 1.62-2.09(m, 4H); 2.23(s, 3H);3.69(s, 3H); 3.78-3.97(m, 2H); 4.15-4.30(m, 3H); 4.45(d, 2H);5.06-5.23(br, 1H); 7.33-7.65(m, 3H) A-445 1.40(t, 3H); 2.25(s, 3H);3.05(q, 2H); 3.69(s, 3H); 4.46(d, 2H); 5.20(br, 1H); 5.31(s, 2H);7.13-7.66(m, 4H)

Now, Preparation Examples of intermediates for the synthesis of thecompound of the present invention will be shown below as ReferenceExamples.

Reference Example 1 Preparation of Methyl4-chloro-3-(methoxycarbonylaminomethyl)benzoate

40.4 g of methyl 4-chloro-3-methylbenzoate, 39 g of N-bromosuccinimideand 1 g of azobisisobutyronitrile were added to 300 ml of carbontetrachloride, followed by reflux under heating for 4 hours. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature, insoluble matters were collected by filtration and thefiltrate was concentrated. The obtained crude crystals were washed withhexane to obtain 34.3 g of methyl 3-bromomethyl-4-chlorobenzoate aswhite crystals.

16.0 g of the obtained methyl 3-bromomethyl-4-chlorobenzoate, 15.0 g ofpotassium cyanate and 35 ml of methanol were added to 200 ml ofN,N-dimethylformamide, followed by stirring at 90° C. for 4 hours. Aftercompletion of the reaction, water was added to the reaction mixture,extraction with ethyl acetate was carried out, and the organic layer wasdried over anhydrous magnesium sulfate. The solvent was distilled offunder reduced pressure, and the obtained crude crystals were washed withisopropanol to obtain 25.2 g of methyl4-chloro-3-(methoxycarbonylaminomethyl)benzoate as white crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 3.70 (s, 3H); 3.90 (s, 3H); 4.48 (d, 2H);5.29 (br, 1H); 7.43 (d, 1H); 7.89 (dd, 1H); 8.05 (s, 1H).

Reference Example 2 Preparation Process of MethylN-(2-chloro-5-hydroxymethylbenzyl)carbamate

10.3 g of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate wasdissolved in 80 ml of anhydrous tetrahydrofuran, 100 ml ofdiisobutylaluminum hydride (0.95 M hexane solution) was dropwise addedthereto in an atmosphere of nitrogen at from −50° C. to −30° C., andafter completion of the dropwise addition, the mixture was stirred atroom temperature for 16 hours. After completion of the reaction, dilutedhydrochloric acid was dropwise added to the reaction mixture at 0° C.,water was added thereto, extraction with ethyl acetate was carried out,and the organic layer was dried over anhydrous magnesium sulfate. Thesolvent was distilled off under reduced pressure, and the residue waspurified by silica gel column chromatography (Wakogel C-200, eluent:hexane/ethyl acetate=1/1) to obtain 6.5 .g of methylN-(2-chloro-5-hydroxymethylbenzyl)carbamate as white crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.20 (br, 1H); 3.67 (s, 3H); 4.43 (d, 2H);4.65 (s, 2H); 5.26 (br, 1H); 7.21-7.37 (m, 3H).

Reference Example 3 Preparation Process of MethylN-(5-bromomethyl-2-chlorobenzyl)carbamate

6.2 g of methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate wasdissolved in 50 ml of ethylene glycol dimethyl ether, and 2.7 g ofphosphorus tribromide was dropwise added to this solution at −20° C.,followed by stirring at room temperature for 1 hour. After completion ofthe reaction, water was added to the reaction solution, extraction withethyl acetate was carried out, followed by washing with an aqueoussodium hydrogencarbonate solution, and the organic layer was dried overanhydrous magnesium sulfate. The solvent was distilled off under reducedpressure to obtain 6.1 g of methylN-(5-bromomethyl-2-chlorobenzyl)carbamate as white crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 3.70 (s, 3H); 4.37 (d, 2H); 4.49 (s, 2H);5.20 (br, 1H); 7.25-7.40 (m, 3H).

Reference Example 4 Preparation of MethylN-(2-chloro-5-cyanomethylbenzyl)carbamate

2.3 g of the methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate obtainedin Reference Example 3 was dissolved in 20 ml of N,N-dimethylformamide,and 0.43 g of sodium cyanide was added thereto at 0° C. Stirring wascarried out at 0° C. for 1 hour, and stirring was carried out furtherfor 4 hours at room temperature, then water was added to the reactionmixture, extraction with ethyl acetate was carried out, and the organicsolvent was dried over anhydrous magnesium sulfate. The solvent wasdistilled off under reduced pressure, and the obtained crude crystalswere washed with hexane to obtain 1.3 g of methylN-(2-chloro-5-cyanomethylbenzyl)carbamate as white crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 3.70 (s, 3H); 3.73 (s, 2H); 4.44 (d, 2H);5.21 (br, 1H); 7.24-7.40 (m, 3H).

Reference Example 5 Preparation of MethylN-(2-chloro-5-acetylbenzyl)carbamate

25.0 g of 4-chloro-3-methylacetophenone, 26.6 g of N-bromosuccinic imideand a catalytic amount of azobisisobutyronitrile were added to 150 ml ofcarbon tetrachloride, followed by reflux under heating for 2 hours.After completion of the reaction, the reaction mixture was cooled toroom temperature, insoluble matters were collected by filtration, andthe filtrate was concentrated under reduced pressure. The obtainedresidue, 18.0 g of potassium cyanate and 38 ml of methanol were added to150 ml of N,N-dimethylformamide, followed by stirring at 90° C. for 4hours. After completion of the reaction, water was added to the reactionmixture, extraction with ethyl acetate was carried out, and the organiclayer was dried over anhydrous magnesium sulfate. The solvent wasdistilled off under reduced pressure, and the obtained residue waspurified by silica gel column chromatography (Wakogel C-200, eluent:hexane/ethyl acetate) and washed with isopropyl ether to obtain 6.8 g ofmethyl N-(2-chloro-5-acetylbenzyl)carbamate as colorless crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.59 (s, 3H); 3.70 (s, 3H); 4.50 (d, 2H);5.31 (br, 1H); 7.46 (d, 1H); 7.81 (dd, 1H); 7.97 (s, 1H).

Reference Example 6 Preparation of MethylN-(2-chloro-5-acetylbenzyl)carbamate

25.0 g of 4-chloro-3-methylacetophenone and 13.9 g oftrichloroisocyanuric acid were suspended in 150 ml of chlorobenzene. Acatalytic amount of azobisisobutyronitrile was added thereto, followedby stirring under heating at from 85 to 90° C. for 12 hours. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature, and insoluble matters were collected by filtration. Thefiltrate was washed with an aqueous sodium hydroxide solution and waterin this order, and the organic layer was dried over anhydrous magnesiumsulfate. The solvent was distilled off under reduced pressure, and theobtained residue, 12.2 g of potassium cyanate and 14.4 g of methanolwere added to 150 ml of N,N-dimethylformamide, followed by stirringunder heating at 90° C. for 4 hours. After completion of the reaction,water was added to the reaction mixture, extraction with ethyl acetatewas carried out, and the organic layer was dried over anhydrousmagnesium sulfate. The solvent was distilled off under reduced pressure,and the obtained residue was purified by silica gel columnchromatography (Wakogel C-200, eluent: hexane/ethyl acetate=3/1). Theobtained crystals were washed with isopropyl ether to obtain 6.0 g ofmethyl N-(2-chloro-5-acetylbenzyl)carbamate as colorless crystals.

¹H-NMR: (CDCl₃/TMS, δ (ppm)); 2.59 (s, 3H); 3.70 (s, 3H); 4.50 (d, 2H);5.31 (br, 1H); 7.46 (d, 1H); 7.81 (dd, 1H); 7.97 (s, 1H).

The agricultural/horticultural fungicides of the present inventioncontain carbamate derivatives represented by the general formula [I] asthe active ingredients. When the compounds of the present invention areused for agricultural/horticultural fungicides, the active ingredientcan be used in appropriate formulations depending on the purpose. Theactive ingredient is usually diluted with an inert liquid or solidcarrier and is used in an appropriate dosage form such as a dust, awettable powder, an emulsifiable concentrate or a granule by blending itwith a surfactant and other ingredients, depending on its use. Theblending proportion of the active ingredient is suitably selecteddepending on the case. However, preferable proportion is from 0.1 to 20%(by weight) in the cases of a dust or a granule, and from 5 to 80% (byweight) in the cases of an emulsifiable concentrate or a wettablepowder.

Preferable examples of carriers include solid carriers such as talc,bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite,slaked lime, silica sand, ammonium sulfate and urea and liquid carrierssuch as isopropyl alcohol, xylene, cyclohexanone and methylnaphthalene.Examples of surfactants and dispersants includedinaphthylmethanesulfonates, alcohol-sulfuric acid ester salts,alkylarylsulfonates, lignin sulfonate, polyoxyethylene glycol ether,polyoxyethylene alkyl aryl ethers and polyoxyethylene sorbitanmonoalkylate. Examples of adjuvants include carboxymethyl cellulose andthe like.

The agricultural/horticultural fungicides of the present invention areapplied after these formulations are diluted or directly for foliagetreatment, seed treatment, soil treatment, paddy water application ornursery box treatment. The dose depends on the type of the compound tobe used, the disease to be controlled, the tendency of diseasedevelopment, the degrees of the damage, the environmental conditions,the type of the formulation to be used and the like. For example, fordirect use as a dust or a granule, the dose of the active ingredient isselected suitably within a range of from 0.1 g to 5 kg, preferably from1 g to 1 kg, per 10 are. For use in a liquid state as an emulsifiableconcentrate or a wettable powder, the dose is selected suitably within arange of from 0.1 ppm to 10,000 ppm, preferably from 10 to 3,000 ppm.

The compound of the present invention in the above formulations cancontrol plant diseases caused by Oomycetes, Ascomycetes, Basidiomycetesand Deuteromycetes. Specific but non-restrictive examples ofmicroorganisms are given below. Pseudoperonospora genus such asPseudoperonospora cubensis, Venturia genus such as Venturia inaequalis,Erysiphe genus such as Erysiphe graminis, Pyricularia genus such asPyricularia oryzae, Botrytis genus such as Botrytis cinerea, Rhizoctoniagenus such as Rhizoctonia solani, Puccinia genus such as Pucciniarecondita, Septoria genus such as Septoria nodorum, and Sclerotinia suchas Sclerotinia sclerotiorum.

The compounds of the present invention can be used in combination withinsecticides, other fungicides, herbicides, plant growth regulators orfertilizers, as the case requires. Now, typical formulations of theagricultural/horticultural fungicides of the present invention will bedescribed with reference to Formulation Examples. Hereinafter, “%” means“% by weight”.

Formulation Example 1 Dust

2% of Compound (A-30), 5% of diatomaceous earth and 93% of clay wereuniformly mixed and pulverized to give a dust.

Formulation Example 2 Wettable Powder

50% of Compound (A-31), 45% of diatomaceous earth, 2% of sodiumdinaphthylmethanedisulfonate and 3% of sodium lignin sulfonate wereuniformly mixed and pulverized to give a wettable powder.

Formulation Example 3 Emulsifiable Concentrate

30% of Compound (A-109), 20% of cyclohexanone, 11% of polyoxyethylenealkyl aryl ether, 4% of calcium alkylbenzenesulfonate and 35% ofmethylnaphthalene were uniformly dissolved to give an emulsifiableconcentrate.

Formulation Example 4 Granule

5% of Compound (A-45), 2% of sodium salt of lauryl alcohol sulfuricester, 5% of sodium lignin sulfonate, 2% of carboxymethyl cellulose and86% of clay were uniformly mixed and pulverized. The resulting mixturewas kneaded with 20% of water, granulated to 14 to 32 mesh by means ofan extrusion granulator and dried to give a granule.

Now, the effects of the agricultural/horticultural fungicides of thepresent invention will be described with reference to specific TestExamples.

Test Example 1 Test for Preventive Effect on Wheat Powdery Mildew

10 Wheat seeds (variety: Norin-61-go) were sown in each plastic pothaving a diameter of 6 cm, and grown in a greenhouse. Wheat seedlingswhich reached a two-leaf stage were treated with 10 ml per pot ofaqueous solutions of wettable powders prepared in accordance withFormulation Example 2, at a concentration of 500 ppm in terms of theactive ingredients, and dried in the air. Then, the seedlings wereinoculated with Erysiphe graminis spore and controlled in a greenhouse.10 Days after the inoculation, the total diseased area of the firstleaves in each pot was observed and evaluated on the basis of thestandards shown in Table 21. The results are shown in Table 22.

TABLE 21 Evaluation A No diseased area B Diseased area of less than 5% CDiseased area of at least 5% but less than 10% D Diseased area of atleast 10%

TABLE 22 Compound No. Evaluation A-3 A A-30 B A-31 B A-37 A A-38 A A-39A A-40 A A-41 B A-42 A A-43 A A-46 A A-49 A A-50 A A-51 A A-55 A A-58 AA-61 A A-62 A A-64 B A-80 A A-81 A A-82 A A-83 A A-84 A A-85 A A-86 AA-87 A A-88 A A-89 A A-90 A A-91 A A-92 A A-98 A A-99 A A-100 A A-101 AA-112 A A-113 A

Test Example 2 Test for Preventive Effect on Septoria Leaf Blotch ofWheat

10 Wheat seeds (variety: Norin-61-go) were sown in each plastic pothaving a diameter of 6 cm, and grown in a greenhouse. Wheat seedlingswhich reached a two-leaf stage were treated with 10 ml per pot ofaqueous solutions of wettable powders prepared in accordance withFormulation Example 2, at a concentration of 50 ppm in terms of theactive ingredients, and dried in the air. Then, the seedlings wereinoculated with Septoria nodorum pycnidia and controlled in agreenhouse. 10 Days after the inoculation, the total diseased area ofthe first leaves in each pot was observed and evaluated on the basis ofthe standards shown in Table 21. The results are shown in Table 23.

TABLE 23 Comp. Evalua- Comp. Evalua- Comp. Evalua- Comp. Evalua- Comp.Evalua- No. tion No. tion No. tion No. tion No. tion A-3 B A-153 A A-291A A-346 A A-398 A A-7 A A-154 A A-293 A A-347 A A-400 B A-8 B A-155 AA-294 B A-348 B A-403 A A-20 B A-156 A A-295 B A-349 A A-404 A A-21 AA-157 A A-296 A A-354 B A-405 A A-51 B A-158 A A-297 B A-355 B A-406 AA-52 A A-159 A A-303 A A-356 A A-407 A A-53 A A-160 B A-304 A A-358 AA-410 A A-54 A A-185 A A-305 A A-359 B A-411 A A-56 B A-189 A A-306 AA-360 A A-412 A A-58 B A-198 A A-309 B A-361 B A-413 A A-61 B A-201 AA-310 A A-362 A A-414 A A-62 B A-206 B A-311 A A-363 A A-415 A A-64 AA-207 A A-312 A A-364 A A-416 A A-70 A A-208 B A-313 A A-365 B A-417 AA-73 A A-215 A A-314 A A-367 A A-418 A A-80 A A-216 A A-315 A A-368 AA-428 A A-81 B A-217 A A-320 A A-369 A A-429 A A-82 B A-218 A A-321 BA-370 A A-430 A A-83 A A-220 A A-322 A A-371 A A-431 A A-85 B A-225 AA-323 A A-372 A A-432 A A-87 B A-227 B A-324 A A-373 A A-433 B A-88 BA-228 B A-325 A A-374 A A-438 B A-89 B A-241 B A-326 A A-375 B A-440 BA-90 A A-242 A A-327 A A-376 B A-441 A A-91 B A-248 B A-328 A A-377 AA-443 B A-92 B A-251 A A-329 A A-378 A A-444 B A-93 A A-252 A A-330 BA-379 A A-94 A A-254 A A-331 A A-380 A A-95 A A-256 A A-332 A A-381 AA-98 A A-257 A A-333 A A-382 B A-99 B A-258 B A-334 A A-384 A A-102 AA-266 B A-338 A A-385 B A-103 B A-269 A A-339 A A-386 B A-111 A A-277 BA-340 B A-387 B A-112 B A-278 B A-341 A A-388 A A-113 A A-279 B A-342 AA-389 A A-150 B A-283 B A-343 A A-392 A A-151 A A-285 A A-344 A A-396 AA-152 A A-286 A A-345 B A-397 A

Test Example 3 Test for Preventive Effect on Cucumber Gray Mold

4 cucumber seeds (variety: Sagami-hanziro) were sown in each plastic pothaving a diameter of 6 cm and grown in a greenhouse. Cucumber youngseedlings which reached a cotyledon stage were treated with 10 ml perpot of aqueous solutions of wettable powders prepared in accordance withFormulation Example 2, at a concentration of 500 ppm in terms of theactive ingredients and dried in the air. Then, the seedlings wereinoculated with Botrytis cinerea spore by putting a paper disc soakedwith the spore suspension on the surface of the cucumber cotyledons, andthe seedlings were immediately placed in a moist chamber of 22° C. 3Days after the inoculation, the total diseased area of the cotyledons ineach pot was observed and evaluated on the basis of the standards shownin Table 24. The results are shown in Table 25.

TABLE 24 Evaluation A No diseased area B Diseased area of less than 25%of the non- treated plot C Diseased area of at least 25% but less than50% of the non-treated plot D Diseased area of at least 50%

TABLE 25 Comp. No. Evaluation A-3 B A-7 B A-37 B A-38 A A-39 B A-40 BA-46 B A-49 B A-50 A A-51 A A-62 B A-81 A A-82 B A-83 B A-84 B A-87 BA-88 B A-90 B A-99 B A-100 B A-112 A A-113 B A-150 B A-157 B A-206 BA-220 B A-225 B A-254 B A-255 B A-256 B A-258 B A-279 B A-285 B A-286 AA-291 3 A-294 A A-295 B A-296 A A-297 B A-300 B A-305 B A-306 A A-309 AA-310 B A-311 B A-312 B A-313 A A-314 A A-315 A A-322 B A-323 A A-324 AA-325 A A-326 A A-327 B A-328 A A-329 B A-330 A A-331 B A-333 B A-334 BA-338 B A-341 B A-342 B A-343 B A-348 A A-355 A A-363 B A-367 B A-370 AA-371 B A-373 B A-375 A A-377 A A-384 B A-396 A A-404 B A-405 B A-406 BA-407 A A-410 B A-412 A A-413 A A-415 A A-416 B A-417 A A-420 A A-424 AA-425 A A-427 A A-428 B A-429 A A-430 A A-432 B A-437 B A-438 B A-443 B

INDUSTRIAL APPLICABILITY

The agricultural/horticultural fungicides of the present invention havehigh controlling effects on cucumber downy mildew, apple scab, wheatpowdery mildew, rice blast, cucumber gray mold, rice sheath blight,wheat brown leaf rust, wheat septoria leaf blotch and cucumber stem rot,and are excellent in residual effectiveness and rain-fastness withoutdamaging crops, and thus they are useful as agricultural/horticulturalfungicides.

What is claimed is:
 1. A carbamate compound represented by formula [I]:

wherein X is a halogen atom, a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group,a C₁-C₆ haloalkyl group or a C₃-C₆ haloalkoxy group, n is 0 or aninteger of from 1 to 4, R¹ is a C₁-C₆ alkyl group, R² is a hydrogenatom, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group,a C₁-C₆ alkoxy group, a C₁-C₆ alkoxy C₁-C₆ alkyl group, a C₁-C₆alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a C₁-C₆ alkylcarbonylC₁-C₆ alkyl group or a benzyl group which may be substituted, R³ is ahydrogen atom or a C₁-C₆ alkyl group, G is an oxygen atom, a sulfur atomor a —NR⁴— group, wherein R⁴ is a hydrogen atom or a C₁-C₆ alkyl group,Y is a hydrogen atom, a C₁-C₁₀ alkyl group said group may be which isoptionally substituted by the same or different at least one halogenatom, cyano group, nitro group, hydroxyl group, C₃-C₆ cycloalkyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ alkylsulfinyl group,carboxyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group,C₁-C₆ alkoxyimino group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ whichare the same or different, is a hydrogen atom or a C₁-C₆ alkyl group, aC₂-C₁₀ alkenyl group which is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group, a C₂-C₁₀ alkynyl group which is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, cycloalkyl group, hydroxyl group, C₁-C₆ alkoxygroup, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylaminogroup, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonylgroup, C₁-C₆ alkoxycarbonyl group, or C(O)NR³R⁶, wherein each of R⁵ andR⁶ which are the same or different, is a hydrogen atom or a C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl group which is optionally substituted by thesame or different at least one halogen atom, cyano group, nitro group,C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group, a C₃-C₆ cycloalkenyl group which isoptionally substituted by the same or different at least one halogenatom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group,hydroxyl group, C₂-C₆ alkynyl group, amino group, mono C₁-C₆ alkylaminogroup, di-C₁-C₆ alkylamino group, C₁-C₆ alkoxy group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, aphenacyl group which is optionally substituted by the same or differentat least one halogen atom, C₁-C₆ alkyl group, C₁-C₆ alkoxy group, C₁-C₆haloalkyl group, C₁-C₆ alkylcarbonyl group or C₁-C₆ alkoxycarbonylgroup, an aryl group which is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, C₁-C₆alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶, whereineach of R⁵ and R⁶ which are the same or different, is a hydrogen atom ora C₁-C₆ alkyl group, a heteroaryl group which is optionally substitutedby the same or different at least one halogen atom, cyano group, nitrogroup, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group,hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylaminogroup, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkylgroup, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, orC(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same or different, isa hydrogen atom or a C₁-C₆ alkyl group, an aryl-C₁-C₆ alkyl group,wherein the aryl in said group is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, C₁-C₆alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, phenoxy groupwhich may be substituted, hydroxyl group, C₁-C₆ alkoxy group, aminogroup, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ haloalkoxy group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, C₁-C₆ alkoxyimino C₁-C₆alkyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the sameor different, and is a hydrogen atom or a C₁-C₆ alkyl group, anaryl-C₁-C₆ alkenyl group wherein the aryl in said group is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₁-C₆ alkenyl group, C₂-C₆alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group or aheterocyclic-C₁-C₆ alkyl group wherein the heterocycle in said group isoptionally substituted by the same or different at least one halogenatom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group,C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group,mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, and Qis a hydrogen atom, a haloalkyl group, a cyano group, a C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl group, a C₁-C₄ alkylthio group, a C₁-C₄alkylsulfinyl group, a C₁-C₄ alkylsulfonyl group or a phenyl group,wherein said group is optionally substituted by at least one halogenatom, cyano group, nitro group, C₁-C₄ alkyl group, C₂-C₄ alkenyl group,C₂-C₄ alkynyl group, hydroxyl group, C₁-C₄ alkoxy group, C₁-C₄ haloalkylgroup, C₁-C₄ haloalkoxy group, C₁-C₄ alkylcarbonyl group or C₁-C₄alkoxycarbonyl group.
 2. The carbamate compound according to claim 1,wherein Y is a hydrogen atom, a substituted C₁-C₁₀ alkyl group which issubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, hydroxyl group, C₃-C₆ cycloalkyl group, C₁-C₆ alkoxygroup, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylaminogroup, C₁-C₆ alkylthio group, C₁-C₆ alkylsulfinyl group, carboxyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, C₁-C₆ alkoxyiminogroup, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same ordifferent, is a hydrogen atom or a C₁-C₆ alkyl group, a C₂-C₁₀ alkenylgroup, wherein said group is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ , which are the same or different, is ahydrogen atom or a C₁-C₆ alkyl group, a C₂-C₁₀ alkynyl group whereinsaid group is optionally substituted by the same or different at leastone halogen atom, cyano group, nitro group, cycloalkyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶, which are the same or different, is ahydrogen atom or a C₁-C₆ alkyl group, a C₃-C₆ cycloalkyl group, whereinsaid group is optionally substituted by the same or different at leastone halogen atom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆alkenyl group, C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group,amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group,C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group,C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶which are the same or different, is a hydrogen atom or a C₁-C₆ alkylgroup, a C₃-C₆ cycloalkenyl group, wherein said group is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, hydroxylgroup, C₂-C₆ alkynyl group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkoxy group, C₁-C₆ alkylthio group,C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonylgroup, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same ordifferent, is a hydrogen atom or a C₁-C₆ alkyl group, a phenacyl group,wherein said group is optionally substituted by the same or different atleast one halogen atom, C₁-C₆ alkyl group, C₁-C₆ alkoxy group, C₁-C₆haloalkyl group, C₁-C₆ alkylcarbonyl group or C₁-C₆ alkoxycarbonylgroup, an aryl group, wherein said group is optionally substituted bythe same or different at least one halogen atom, cyano group, nitrogroup, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group,hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylaminogroup, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkylgroup, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, orC(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same or different, isa hydrogen atom or a C₁-C₆ alkyl group, a heteroaryl group, wherein saidgroup is optionally substituted by the same or different at least onehalogen atom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenylgroup, C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, aminogroup, mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, anaryl-C₁-C₆ alkyl group, wherein the aryl in said group is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, phenoxy group which may be substituted, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆haloalkoxy group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group,C₁-C₆ alkoxyimino C₁-C₆ alkyl group, or C(O)NR⁵R⁶, wherein each of R⁵and R⁶ which are the same or different, is a hydrogen atom or a C₁-C₆alkyl group, an aryl-C₂-C₆ alkenyl group, wherein the aryl in said groupis optionally substituted by the same or different at least one halogenatom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group,C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group,mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group or aheterocyclic-C₁-C₆ alkyl group, wherein the heterocycle in said group isoptionally substituted by the same or different at least one halogenatom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group,C₂-C₆ alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group,mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group.
 3. Thecarbamate compound according to claim 1, wherein Y is a hydrogen atom, aC₂-C₁₀ alkenyl group, wherein said group is optionally substituted bythe same or different at least one halogen atom, cyano group, nitrogroup, hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group,C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonylgroup, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same ordifferent, is a hydrogen atom or a C₁-C₆ alkyl group, a C₂-C₁₀ alkynylgroup, wherein said group is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group,cycloalkyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group or C(O)NR⁵R⁶ wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, aC₃-C₆ cycloalkyl group, wherein said group is optionally substituted bythe same or different at least one halogen atom, cyano group, nitrogroup, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group,hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylaminogroup, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkylgroup, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, orC(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same or different, isa hydrogen atom or a C₁-C₆ alkyl group, a C₃-C₆ cycloalkenyl group, saidgroup is optionally substituted by the same or different at least onehalogen atom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenylgroup, hydroxyl group, C₂-C₆ alkynyl group, amino group, mono C₁-C₆alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkoxy group, C₁-C₆alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, aphenacyl group, wherein said group is optionally substituted by the sameor different at least one halogen atom, C₁-C₆ alkyl group, C₁-C₆ alkoxygroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group or C₁-C₆alkoxycarbonyl group, an aryl group, wherein said group is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, hydroxyl group, C₁-C₆ alkoxy group, amino group, monoC₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ alkylcarbonyl group, C₁-C₆alkoxycarbonyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which arethe same or different, is a hydrogen atom or a C₁-C₆ alkyl group, aheteroaryl group, wherein said group is optionally substituted by thesame or different at least one halogen atom, cyano group, nitro group,C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group, an aryl-C₁-C₆ alkyl group, wherein the arylin said group is optionally substituted by the same or different atleast one halogen atom, cyano group, nitro group, C₁-C₆ alkyl group,C₂-C₆ alkenyl group, C₁-C₆ alkynyl group, phenoxy group which isoptionally substituted, hydroxyl group, C₁-C₆ alkoxy group, amino group,mono C₁-C₆ alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthiogroup, C₁-C₆ haloalkyl group, C₁-C₆ haloalkoxy group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, C₁-C₆ alkoxyimino C₁-C₆alkyl group, or C(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the sameor different, is a hydrogen atom or a C₁-C₆ alkyl group, an aryl-C₂-C₆alkenyl group wherein the aryl in said group is optionally substitutedby the same or different at least one halogen atom, cyano group, nitrogroup, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group,hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylaminogroup, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkylgroup, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, orC(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same or different, isa hydrogen atom or a C₁-C₆ alkyl group or a heterocyclic-C₁-C₆ alkylgroup the heterocycle in said group is optionally substituted by thesame or different at least one halogen atom, cyano group, nitro group,C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group.
 4. The carbamate compound according toclaim 1, wherein Y is an aryl-C₁-C₆ alkyl group, wherein the aryl insaid group may be substituted by the same or different at least onehalogen atom, cyano group, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenylgroup, C₂-C₆ alkynyl group, phenoxy group which is optionallysubstituted, hydroxyl group, C₁-C₆ alkoxy group, amino group, mono C₁-C₆alkylamino group, di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group,C₁-C₆ haloalkyl group, C₁-C₆ haloalkoxy group, C₁-C₆alkylcarbonyl group,C₁-C₆ alkoxycarbonyl group, C₁-C₆ alkoxyimino C₁-C₆ alkyl group, orC(O)NR⁵R⁶, wherein each of R⁵ and R⁶ which are the same or different, isa hydrogen atom or a C₁-C₆ alkyl group.
 5. The carbamate compoundaccording to claim 1, wherein Y is a heterocyclic-C₁-C₆ alkyl group,wherein the heterocycle in said group is optionally substituted by thesame or different at least one halogen atom, cyano group, nitro group,C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group.
 6. The carbamate compound according toclaim 1, wherein Y is a heteroaryl-C₁-C₆ alkyl group, wherein theheteroaryl in said group is optionally substituted by the same ordifferent at least one halogen atom, cyano group, nitro group, C₁-C₆alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxyl group,C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group, di-C₁-C₆alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group, C₁-C₆alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group, or C(O)NR⁵R⁶, whereineach of R⁵ and R⁶ which are the same or different, is a hydrogen atom ora C₁-C₆ alkyl group.
 7. The carbamate compound according to claim 1,wherein Y is a benzyl group, wherein said group is optionallysubstituted by the same or different at least one halogen atom, cyanogroup, nitro group, C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆alkynyl group, phenoxy group which is optionally substituted, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ haloalkoxy group, C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonylgroup, C₁-C₆ alkoxyimino C₁-C₆ alkyl group, or C(O)NR⁵R⁶, wherein eachof R⁵ and R⁶ which are the same or different, is a hydrogen atom or aC₁-C₆ alkyl group or a heteroaryl-C₁-C₆ alkyl group represented by afive- to six-membered cycle containing at least one nitrogen atomwherein the heteroaryl in said group is optionally substituted by thesame or different at least one halogen atom, cyano group, nitro group,C₁-C₆ alkyl group, C₂-C₆ alkenyl group, C₂-C₆ alkynyl group, hydroxylgroup, C₁-C₆ alkoxy group, amino group, mono C₁-C₆ alkylamino group,di-C₁-C₆ alkylamino group, C₁-C₆ alkylthio group, C₁-C₆ haloalkyl group,C₁-C₆ alkylcarbonyl group, C₁-C₆ alkoxycarbonyl group or C(O)NR⁵R⁶,wherein each of R⁵ and R⁶ which are the same or different, is a hydrogenatom or a C₁-C₆ alkyl group.
 8. An agricultural/horticultural fungicidecomposition, comprising: the carbamate derivative as defined claim 1 asthe active ingredient and a fungicidally acceptable carrier.
 9. Theagricultural/horticultural fungicide composition according to claim 8,wherein the composition, formulated as a dust or granules, contains from0.1 to 20% by weight of the active ingredient.
 10. Theagricultural/horticultural fungicide composition according to claim 8,wherein the composition, formulated as an emulsifiable concentrate or awettable powder, contains from 5 to 80% by weight of the activeingredient.
 11. The agricultural/horticultural fungicide compositionaccording to claim 8, wherein the carrier is a solid carrier selectedfrom the group consisting of talc, bentonite, clay, kaolin, diatomaceousearth, white carbon, vermiculite, slaked lime, silica sand, ammoniumsulfate and urea.
 12. The agricultural/horticultural fungicidecomposition according to claim 8, wherein the carrier is a liquidcarrier selected from the group consisting of isopropyl alcohol, xylene,cyclohexanone and methylnaphthalene.
 13. The agricultural/horticulturalfungicide composition according to claim 8, wherein the composition isformulated with a surfactant or dispersant selected from the groupconsisting of dinaphthylmethanesulfonate, alcohol sulfuric acid estersalts, alkylarylsulfonates, lignin sulfonate, polyoxyethylene glycolether, polyoxyethylene alkyl aryl ether and polyoxyethylene sorbitanmonoalkylate.